Trifluoroacetic acid → (1R,3S,5R)-2-Aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoro methoxy-phenyl)-amide trifluoroacetate

HRID 1527599Notes

Reaction equation

HRID 1527599 reaction equation
C(OC([N:8]1[C@H:13]([C:14](=[O:28])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[C:17]=2[F:27])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=O)(C)(C)C.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]>C(Cl)Cl>[F:32][C:31]([F:34])([F:33])[C:29]([OH:35])=[O:30].[F:27][C:17]1[C:18]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:14]([C@@H:13]1[CH2:12][C@@H:11]2[C@@H:9]([CH2:10]2)[NH:8]1)=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283686(1R,3S,5R)-3-(2-Fluoro-3-trifluoromethoxy-phenylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Product 1

HCID 86673879(1R,3S,5R)-2-Aza-bicyclo[3.1.0]hexane-3-carboxylic acid (2-fluoro-3-trifluoro methoxy-phenyl)-amide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((1R,3S,5R)-3-(2-fluoro-3-trifluoromethoxy-phenylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (2.56 g, 6.33 mmol) in CH2Cl2 (20 mL) was added TFA (10 mL, 130 mmol) and the solution was stirred at RT for 16 h. CH2Cl2 was concentrated, the residue was suspended in MeOH, concentrated again and dried under high vacuum to give the desired material which was used without further purification in the next step. MS: 305 [M+H]+; tR (HPLC conditions c): 3.55 min.

Workup

  1. concentrationCH2Cl2 was concentrated
  2. concentrationconcentrated again
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-c0db9e3e4a684c44b693303b39c736a0
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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