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5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione
- CAS No.: 764667-64-3
- Purity: 99%
Manufacturer supply high quality 5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione 764667-64-3 with GMP standards
- Molecular Formula: C14H11F3O5
- Molecular Weight: 316.234
- Melting Point: 117 °C (decomp)
- Refractive Index: 1.523
- Boiling Point: 489.0±45.0 °C(Predicted)
- PKA: 4.50±1.00(Predicted)
- PSA： 72.83000
- Density: 1.462±0.06 g/cm3(Predicted)
- LogP: 2.29460
5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione(Cas 764667-64-3) Usage
|
Application |
5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene] is an intermediate for the synthesis of sitagliptin. Sitagliptin is a new type of anti-type II diabetes drug approved by the FDA and the first dipeptidyl peptidase-IV inhibitor drug for the treatment of type II diabetes. |
InChI:InChI=1/C14H11F3O5/c1-14(2)21-12(19)11(13(20)22-14)10(18)4-6-3-8(16)9(17)5-7(6)15/h3,5,18H,4H2,1-2H3
764667-64-3 Relevant articles
Preparation method of sitagliptin phosphate intermediate
-
Paragraph 0028-0029; 0032-0037, (2021/11/21)
The invention discloses a preparation me...
Preparation method of chiral 4 - aryl - β β-amino acid derivative
-
Paragraph 0026-0028, (2021/11/14)
Provided is a method for preparing a chi...
Two methods for the preparation of sitagliptin phosphate: Via chemical resolution and asymmetric hydrogenation
Ye, Fei,Zhang, Zhifeng,Zhao, Wenxia,Ding, Jianhai,Wang, Yali,Dang, Xueyan
, p. 4805 - 4809 (2021/02/03)
Two effective processes have been develo...
NEW EFFICIENT PROCESS FOR THE PREPARATION OF SITAGLIPTIN.
-
Paragraph 0173, (2019/09/06)
Object of the present invention is an ef...
764667-64-3 Process route
-
-
2033-24-1
cycl-isopropylidene malonate
-
-
209995-38-0
(2,4,5-trifluorophenyl)acetic acid
-
-
764667-64-3
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions
| Conditions | Yield |
|---|---|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 45 ℃;
for 3h;
|
95%
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 45 ℃;
for 6h;
|
95%
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 20 - 50 ℃;
|
94%
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 45 - 55 ℃;
|
94%
|
|
cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid;
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 20 - 50 ℃;
for 2 - 3h;
With
hydrogenchloride;
In
acetonitrile;
at 0 ℃;
for 1h;
|
88%
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
1,1'-carbonyldiimidazole;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 3h;
cycl-isopropylidene malonate;
In
tetrahydrofuran;
at 20 ℃;
for 16h;
|
88%
|
|
With
1,1'-carbonyldiimidazole;
In
tetrahydrofuran;
at 50 ℃;
for 5h;
|
87%
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 20 ℃;
for 0.75h;
Cooling with ice;
cycl-isopropylidene malonate;
In
acetonitrile;
at 45 ℃;
|
85%
|
|
With
1,1'-carbonyldiimidazole;
In
tetrahydrofuran;
at 51 ℃;
for 3.08333h;
|
80%
|
|
In
acetonitrile;
at 0 - 45 ℃;
Inert atmosphere;
|
80.7%
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
1,1'-carbonyldiimidazole;
In
tetrahydrofuran;
at 25 - 30 ℃;
cycl-isopropylidene malonate;
In
tetrahydrofuran;
at 50 - 55 ℃;
for 6h;
|
65%
|
|
With
1,1'-carbonyldiimidazole;
In
tetrahydrofuran;
at 50 ℃;
for 5h;
|
60.1%
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
1,1'-carbonyldiimidazole;
In
tetrahydrofuran;
at 25 - 30 ℃;
cycl-isopropylidene malonate;
In
tetrahydrofuran;
at 50 - 55 ℃;
for 6h;
|
60%
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
ISOPROPYLAMIDE;
at 0 - 40 ℃;
for 2 - 3h;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
ISOPROPYLAMIDE;
at 0 - 5 ℃;
for 2 - 3h;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
ISOPROPYLAMIDE;
at 0 - 5 ℃;
for 1h;
|
|
|
cycl-isopropylidene malonate; (2,4,5-trifluorophenyl)acetic acid;
With
dmap; N-ethyl-N,N-diisopropylamine;
In
ISOPROPYLAMIDE;
at 20 - 40 ℃;
With
pivaloyl chloride;
In
ISOPROPYLAMIDE;
at 0 - 5 ℃;
for 2 - 3h;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
N,N-dimethyl acetamide;
at 0 - 40 ℃;
for 2 - 3h;
|
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
oxalic acid; N,N-dimethyl-formamide;
In
dichloromethane;
at 25 - 30 ℃;
for 2 - 3h;
cycl-isopropylidene malonate;
With
dmap;
In
dichloromethane;
at -5 - 0 ℃;
|
|
|
With
pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
dmap;
In
ISOPROPYLAMIDE;
at 0 - 40 ℃;
for 2 - 3h;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 20 - 55 ℃;
for 3 - 5h;
|
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
oxalic acid;
In
dichloromethane; N,N-dimethyl-formamide;
at 25 - 30 ℃;
cycl-isopropylidene malonate;
With
dmap;
In
dichloromethane; N,N-dimethyl-formamide;
at -5 - 0 ℃;
|
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
oxalic acid;
In
dichloromethane; N,N-dimethyl-formamide;
at 25 - 30 ℃;
cycl-isopropylidene malonate;
With
dmap;
In
dichloromethane;
at -5 ℃;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
acetonitrile;
at 20 - 50 ℃;
for 2h;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
N,N-dimethyl acetamide;
for 1h;
Cooling with ice;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
ISOPROPYLAMIDE;
at 0 - 40 ℃;
for 2 - 3h;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
ISOPROPYLAMIDE;
at 5 ℃;
for 2 - 3h;
|
|
|
(2,4,5-trifluorophenyl)acetic acid;
With
dmap; 1,1'-carbonyldiimidazole;
In
tetrahydrofuran;
at 30 ℃;
for 3h;
cycl-isopropylidene malonate;
In
tetrahydrofuran;
at 50 ℃;
for 7h;
Temperature;
|
|
|
With
dmap; pivaloyl chloride; N-ethyl-N,N-diisopropylamine;
In
N,N-dimethyl acetamide;
at 5 - 40 ℃;
for 3h;
Inert atmosphere;
|
-
-
2033-24-1
cycl-isopropylidene malonate
-
-
1176895-65-0
2-(2,4,5-trifluorophenyl)acetyl chloride
-
-
764667-64-3
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Conditions
| Conditions | Yield |
|---|---|
|
With
collidine;
In
dichloromethane;
at -5 - 0 ℃;
for 4h;
Product distribution / selectivity;
Inert atmosphere;
|
|
|
cycl-isopropylidene malonate; 2-(2,4,5-trifluorophenyl)acetyl chloride;
In
dichloromethane;
at -5 - 30 ℃;
for 4h;
Inert atmosphere;
With
hydrogenchloride;
In
dichloromethane; water;
at 0 - 5 ℃;
Product distribution / selectivity;
|
764667-64-3 Upstream products
-
2033-24-1
cycl-isopropylidene malonate
-
209995-38-0
(2,4,5-trifluorophenyl)acetic acid
-
1176895-65-0
2-(2,4,5-trifluorophenyl)acetyl chloride
-
86393-34-2
2,4-dichloro-5-fluorobenzoyl chloride
764667-64-3 Downstream products
-
764667-65-4
1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butane-1,3-dione
-
769195-26-8
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
-
881995-69-3
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
-
881995-73-9
3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
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