Ethanol → HCID 66657250, compound

HRID 660111Notes

Reaction equation

HRID 660111 reaction equation
C(O)C.[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([N:16]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([Cl:35])[CH:29]=2)[C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=2)[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[OH-].[Na+].ClCCl>C(O)(=O)C>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([N:16]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][CH:22]=2)[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([Cl:35])[CH:29]=2)[CH2:12]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 66657186HCID 66657186, compound

Product 1

HCID 66657250HCID 66657250, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To an ethanol solution containing 1.7 g of 3(S)-[(3-chloro-4-fluorophenyl)-(4-ethoxycarbonylphenyl)amino]pyrrolidine-1-carboxylic acid tert-butyl ester (3.7 mmol) was added 6 ml of a 5 N sodium hydroxide solution, followed by stirring at room temperature for 15 hours. Dichloromethane and acetic acid were added to the reaction solution to make the reaction solution acidic. After washing with water three times and with an aqueous saturated sodium hydrogencarbonate solution once, the solvent was distilled off under reduced pressure to thereby obtain 1.50 g of white powdery 3(S)-[(4-carboxyphenyl)-(3-chloro-4-fluorophenyl)amino]pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. washAfter washing with water three times and with an aqueous saturated sodium hydrogencarbonate solution once
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ffdadcc4f82c460387ef1d1d374f2530
Source dataset
uspto-grants-2011_12
Patent number
US08084442B2

Reaction notes

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