Trifluoroacetic acid → (2S,3S,4S)-4-Fluoro-3-methoxy-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate

HRID 1527411Notes

Reaction equation

HRID 1527411 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC([N:15]1[CH2:19][C@H:18]([F:20])[C@@H:17]([O:21][CH3:22])[C@H:16]1[C:23](=[O:34])[NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[F:33])=O)(C)(C)C>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[Cl:32][C:28]1[C:27]([F:33])=[C:26]([CH:31]=[CH:30][CH:29]=1)[CH2:25][NH:24][C:23]([C@@H:16]1[C@H:17]([O:21][CH3:22])[C@@H:18]([F:20])[CH2:19][NH:15]1)=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283934(2S,3S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-3-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86673852(2S,3S,4S)-4-Fluoro-3-methoxy-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.86 mL, 11.12 mmol) was added to a solution of (2S,3S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-3-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester (450 mg, 1.12 mmol) in CH2Cl2 (20 mL). The reaction mixture was stirred overnight then was concentrated. The residue was triturated with Et2O (10 mL) to give a precipitate which was filtered off, washed with Et2O (10 mL) then dried under high vacuum. The absolute stereochemistry was confirmed by X-ray. tR (HPLC conditions f): 0.40 min; MS (UPLC): 349 [M+HCOO]−, 305 [M+H]+.

Workup

  1. concentrationthen was concentrated
  2. customThe residue was triturated with Et2O (10 mL)
  3. customto give a precipitate which
  4. filtrationwas filtered off
  5. washwashed with Et2O (10 mL)
  6. customthen dried under high vacuum
  7. custom0.40 min

Sources & evidence

ORD record
ord-aa3c3d08847c4258a67a1d9e300778c4
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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