Triethylamine → 3-Amino-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (3-chloro-5-fluorobenzyl)amide

HRID 339605

Reaction equation

HRID 339605 reaction equation
CCN(CC)CC.C(S)(S)CC.[Cl:13][C:14]1[CH:15]=[C:16]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:17][NH:18][C:19]([C:21]1([N:33]=[N+]=[N-])[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]1=[O:32])=[O:20]>CO>[Cl:13][C:14]1[CH:15]=[C:16]([CH:36]=[C:37]([F:39])[CH:38]=1)[CH2:17][NH:18][C:19]([C:21]1([NH2:33])[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]1=[O:32])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64285461,1-PropanedithiolHCID 867009653-Azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (3-chloro-5-fluorobenzyl)amide

Product 1

HCID 867009643-Amino-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (3-chloro-5-fluorobenzyl)amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Et3N (0.1 ml, 0.75 mmol) followed by propanedithiol (0.08 ml, 0.75 mmol) are added to a solution of 3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (3-chloro-5-fluorobenzyl)amide (100 mg, 0.25 mmol) in 2 ml of methanol. The batch is stirred at RT for 12 hours. When the reaction is complete, all volatile constituents are removed in vacuo, and the residue is purified on silica gel.

Workup

  1. customall volatile constituents are removed in vacuo
  2. customthe residue is purified on silica gel

Sources & evidence

ORD record
ord-6d31dbd699b44efcac635c3acb941423
Source dataset
uspto-grants-2014_11
Patent number
US08895535B2

Linked notes

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