| Identification | Back Directory | [Name]
(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester | [CAS]
401564-36-1 | [Synonyms]
Teneint-G
Tenaligliptin
Teneligptin interMediate-1
Teneligliptin Intermediate
Teneligptin interMediate B
Teneliglitpin intermediates
Teneligliptin Intermediate-1
Ethyl(2)-chloro[(4-methoxyphenyl)hydrazono]ethanoate
(S)-1-Boc-5-(thiazolidine-3-carbonyl)pyrrolidin-3-one
4-oxo-2-(3-thiazolidinylcarbonyl)-,1,1-dimethylethylester
1-Pyrrolidinecarboxylic acid, 4-oxo-2-(3-thiazolidinylcarbon...
(2S)-4-oxo-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate
tert-butyl 4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate
(S)-tert-Butyl4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylat
(S)-tert-butyl 4-oxo-2-(thiazolidine-3-carbonyl)pyrolidine-1-carboxylate
(S)-tert-butyl 3-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate
(S)-tert-Butyl 4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate
tert-butyl (S)-4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate
3-((S)-1-tert-butoxycarbonyl-4-oxo-2-pyrrolidinylcarbonyl)-1,3-thiazolidine
tert-butyl (2S)-4-oxo-2-(1,3-thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate
(2S)-tert-butyl 4-hydroxy-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate
tert-butyl(2s)-4-oxo-2-(1,3-thiazolidin-3-yl carbonyl) pyrrolidine-1-carboxylate
(2S) -4-oxo-2- (3-thiazolylcarbonyl) -1-pyrrolidine carboxylate tert butyl ester
Tert-butyl (2S) -4-oxo-2-(1,3-Thiazoldine-3yl carboxyl) pyrrolidine-1-carboxylate
(2S)-4-Oxo-2-(thiazolidine-3-carbonyl)-pyrrolidine-1-carboxylic acid t-butyl ester
(2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidincarbaxilic acid tert-butyl ester
(2S)-4-Oxo-2-(thiazolidine-3-carbonyl)-pyrrolidine-1-carboxylic acidtert-butylester
(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
(2S)-4-oxo-2-(1,3-thiazolidin- 3-yIcarbonyI)pyrroIidine
carboxylic acid tert butyl ester
1-Pyrrolidinecarboxylic acid, 4-oxo-2-(3-thiazolidinylcarbonyl)-, 1,1-diMethylethyl ester, (2S)-
(2S) -4-oxo-2- (3-thiazolidinylcarbonyl)
-1-Pyrrolidinecarboxylic acid tert-butyl ester / triliptin intermediate
Tenteligliptin impurity 1
(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester | [EINECS(EC#)]
813-401-8 | [Molecular Formula]
C13H20N2O4S | [MDL Number]
MFCD22665915 | [MOL File]
401564-36-1.mol | [Molecular Weight]
300.37 |
| Chemical Properties | Back Directory | [Boiling point ]
492℃ | [density ]
1.305 | [Fp ]
251℃ | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-1.22±0.20(Predicted) | [color ]
Pale Yellow to Light Yellow | [InChI]
InChI=1S/C13H20N2O4S/c1-13(2,3)19-12(18)15-7-9(16)6-10(15)11(17)14-4-5-20-8-14/h10H,4-8H2,1-3H3/t10-/m0/s1 | [InChIKey]
ULXKZRPRLJGLDM-JTQLQIEISA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC(=O)C[C@H]1C(N1CCSC1)=O |
| Hazard Information | Back Directory | [Uses]
(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester is an intermediate used to prepare dipeptidyl peptidase IV (DPP-IV) inhibitors. | [Synthesis]
To (2S)-1-tertbutyloxycarbonyl-4-oxa-tetramethyleneimine-2-carboxylic
acid (60.0kg), thiazolidine (30.3kg) and the solution
of N-diisopropylethylamine (118kg) in ethyl acetate (595kg), adds the
solution of 28w% propyl phosphonous acid anhydride (cyclic trimer)
in ethyl acetate (446kg) at 2 ℃-7 ℃, and reaction mixture is stirred 2
hours at 2 ℃-4 ℃.To this reaction mixture, add 15w% aqueous citric acid
solution (600kg) for distributing, and ethyl acetate for water layer
(271kg) is extracted.
The ethyl acetate layer obtaining is mixed, and use
successively 10w% ammonium dibasic phosphate aqueous solution (600kg)
and water (300kg) washing. Ethyl acetate layer is concentrated into
residual quantity 300L, normal heptane (739kg), 23 ℃ of-25 ℃ of
interpolations, and is stirred this mixture 1 hour at 23 ℃-25 ℃, and
stir 2 hours at 1 ℃-5 ℃.
The crystal of precipitation is collected by
filtration, is used normal heptane (164kg) washing drying under reduced
pressure to produce (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (67.8kg, yield 86%).
| [References]
[1] Patent: CN103649055, 2016, B. Location in patent: Paragraph 0144-0147
[2] Patent: WO2015/19238, 2015, A1. Location in patent: Page/Page column 9; 10
[3] Patent: WO2016/79699, 2016, A1. Location in patent: Page/Page column 12 |
|
|