Trifluoroacetic acid → (1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

HRID 1917345Notes

Reaction equation

HRID 1917345 reaction equation
C([O:5][C:6]([C@:8]12[CH2:15][CH:14]([F:16])[CH2:13][C@H:12]1[C:11](=[O:17])[N:10]([C@@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[CH2:9]2)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:16][CH:14]1[CH2:15][C@@:8]2([C:6]([OH:7])=[O:5])[C@H:12]([C:11](=[O:17])[N:10]([C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])[CH2:9]2)[CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67491056(1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester

Product 1

HCID 67490956(1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R,5R)-7-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octan-1-ylcarboxylic acid tert-butyl ester (705 mg, 2.03 mmol) was dissolved in methylene chloride (4 mL). Trifluoroacetic acid (4 mL) was added under ice-cooling, and then the mixture was stirred at room temperature for one hour. The reaction solution was concentrated under reduced pressure. Toluene was added to the residue, and the mixture was concentrated under reduced pressure again to give 595 mg (quantitative) of the title compound as a white solid.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionToluene was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure again

Sources & evidence

ORD record
ord-68e2c99235874cdaa4ec28511b326420
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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