| Identification | Back Directory | [Name]
(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile | [CAS]
207557-35-5 | [Synonyms]
cas:207557-35-5
Vigliptin Impurity 14
Vogliptin impurity II
vildagliptin Impurity J
Vildagliptin interMediates
-2-pyrrolidinecarbonitrile
Vildagliptin Intermediate 2
Vildagliptin interMediate C
(R)-hexahydroindolizin-7(1H)-one
1-CHLOROACETYL-2-(S)-CYANOPYRROLIDINE
(S)-2-cyanopyrrolidine-1-carbonyl chlo
2S-1-(2-Chloroacetyl)-2-9-pyrrolidinec
(S)-1-(Chloroacetyl)-2-cyanopyrrolidine
Vildagliptin Chloroacetyl Nitrile Impurity
(S)-2-cyanopyrrolidine-1-carbonyl chloride
Vildagliptin Chloroacetyl Nitrile (S)-Isomer
(2S)-1-CHLOROACETYLPYRROLIDINE-2-CARBONITRILE
(S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile
(2S) -N-chloroacetyl-2-cyano-tetrahydropyrrole
2S)-N-(Chloroacetyl)-2-Pyrrolidine Carbonitrile
(2S)-1-(CHLOROACETYL)-2-PYRROLIDINECARBONITRILE
(S)-1-(2-CHLOROACETYL)PYRROLIDINE-2-CARBONITRILE
1-(2-Chloroacetyl)-pyrrolidine-(2S)-carbonitrile
(2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile
(2S)-1-(2-chloroacetyl)-2-Pyrrolidinecarbonitrile
(2S)-1-(2-Chloroacetyl)-2-9-pyrrolidinecarbonitrile
2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2S)-
2-Pyrrolidinecarbonitrile, 1-(2-chloroacetyl)-, (2S)-
(2S)-1-chloroacetyl-2-pyrrolidine carbonitrile CAS No.
2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2S)- (9CI)
(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile
(Vildagliptin)
(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile ISO 9001：2015 REACH
Vildagliptin Impurity，(2S)-1-(Chloroacetyl)-2- pyrrolidinecarbonitrile
(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile (2S)-1-(2-Chloroacetyl)-2-9-pyrrolidinecarbonitrile
Vildagliptin Impurity 16/Vildagliptin Chloroacetyl Nitrile (S)-Isomer/(2S)-1-(Chloroacetyl)-2-Pyrrolidinecarbonitrile | [EINECS(EC#)]
807-388-8 | [Molecular Formula]
C7H9ClN2O | [MDL Number]
MFCD08689902 | [MOL File]
207557-35-5.mol | [Molecular Weight]
172.61 |
| Chemical Properties | Back Directory | [Melting point ]
52-53 °C | [Boiling point ]
363.1±37.0 °C(Predicted) | [density ]
1.27±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-4.65±0.40(Predicted) | [color ]
Pale Yellow to Light Brown | [Optical Rotation]
Consistent with structure | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C7H9ClN2O/c8-4-7(11)10-3-1-2-6(10)5-9/h6H,1-4H2/t6-/m0/s1 | [InChIKey]
YCWRPKBYQZOLCD-LURJTMIESA-N | [SMILES]
N1(C(CCl)=O)CCC[C@H]1C#N |
| Hazard Information | Back Directory | [Chemical Properties]
White crystals | [Uses]
(2S)-1-(2-Chloroacetyl)-2-9-pyrrolidinecarbonitrile is a key intermediate for dipeptidyl peptidase IV inhibitor Vildagliptin (V305000). | [Synthesis]
A method for the preparation of (S)-1-(2-chloroacetyl)-2-cyanopyrrolidine comprising the steps of dissolving L-prolinamide (0.175 mol) and potassium carbonate (0.348 mol) in 400 mL of acetonitrile, and slowly adding 16 mL (0.2 mol) of chloroacetyl chloride dropwise (dropwise time of 2-3 hrs.) at 0-15°C. After the dropwise addition, the reaction mixture was stirred overnight at room temperature and the reaction was monitored by TLC until complete. Upon completion of the reaction, the mixture was stirred at 0-15°C and 13.4 mL to 0.094 mol of 44 was slowly added, followed by stirring at 25°C overnight and again the reaction was confirmed complete by TLC. Subsequently, the reaction solution was rotary evaporated to dryness and 20 mL of ethyl acetate was added to the residue. An excess of trifluoroacetic anhydride (TFAA) was added to the reaction vessel, and the residue was dissolved in 150 mL of ethyl acetate and the pH was adjusted with sodium carbonate solution to 8. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting oil was left overnight to cure (if not cured, crystalline species could be added), resulting in a light brown solid (target compound) in 92% yield. | [References]
[1] Patent: CN106045891, 2016, A. Location in patent: Paragraph 0046; 0047-0049
[2] Patent: CN105523985, 2016, A. Location in patent: Paragraph 0054; 0055
[3] Patent: CN107501154, 2017, A. Location in patent: Paragraph 0068-0108
[4] Patent: US2008/167479, 2008, A1. Location in patent: Page/Page column 5
[5] Patent: US6432969, 2002, B1 |
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