Trifluoroacetic acid → 3-Chloro-4-fluoro-5-{[((2S,4R)-4-fluoro-pyrrolidine-2-carbonyl)-amino]-methyl}-benzoic acid

HRID 1527363Notes

Reaction equation

HRID 1527363 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([F:13])[CH2:10][C@H:9]1[C:14](=[O:28])[NH:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[C:19]([Cl:26])[C:18]=1[F:27])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:26][C:19]1[CH:20]=[C:21]([CH:22]=[C:17]([CH2:16][NH:15][C:14]([C@@H:9]2[CH2:10][C@@H:11]([F:13])[CH2:12][NH:8]2)=[O:28])[C:18]=1[F:27])[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283054(2S,4R)-2-(5-Carboxy-3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 682835283-Chloro-4-fluoro-5-{[((2S,4R)-4-fluoro-pyrrolidine-2-carbonyl)-amino]-methyl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2S,4R)-2-(5-carboxy-3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (146 mg, 0.3 mmol) in CH2Cl2 (4 mL) was added TFA (1 mL). The reaction mixture was stirred for 1 h at ambient temperature and the solvent was removed in vacuo to give the title compound which was used without further purification. tR (HPLC conditions c): 3.11 min.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-921c5080a1644c6cb0fa781199213030
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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