Trifluoroacetic acid → Trifluoroacetic acid

HRID 1527560Notes

Reaction equation

HRID 1527560 reaction equation
C(OC([N:8]1[C@H:13]([C:14](=[O:25])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[F:24])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=O)(C)(C)C.[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>C(Cl)Cl>[Cl:23][C:19]1[C:18]([F:24])=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][NH:15][C:14]([C@@H:13]1[CH2:12][C@@H:11]2[C@@H:9]([CH2:10]2)[NH:8]1)=[O:25].[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283968HCID 68283968, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 68283681HCID 68283681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3S,5R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (6.35 g, 17.22 mmol) in CH2Cl2 (60 mL) was added TFA (13.18 mL, 172 mmol) and the solution was stirred at RT for 3 h. The crude reaction mixture was concentrated under vacuum, Et2O was added and the white precipitate was filtered off to give the desired compound as a TFA salt. MS (LC/MS): 287.0 [M+H]+, 285.1 [M−H]−; tR (HPLC conditions f) 1.27 min.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under vacuum, Et2O
  3. additionwas added
  4. filtrationthe white precipitate was filtered off

Sources & evidence

ORD record
ord-76a99a38d9ce4d0a93e12d7482241438
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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