Trifluoroacetic acid → Trifluoroacetic acid

HRID 1295380Notes

Reaction equation

HRID 1295380 reaction equation
C(OC(=O)[NH:7][C@@:8]12[CH2:13][CH:12]1[CH2:11][N:10]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[C@H:9]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(C)(C)C.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>C(Cl)Cl>[NH2:7][C@@:8]12[CH2:13][CH:12]1[CH2:11][N:10]([C:14](=[O:19])[C:15]([F:16])([F:17])[F:18])[C@H:9]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86602064HCID 86602064, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 86602065HCID 86602065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A flask containing the racemic Intermediate 53, one enatiomer being [(1S,2S)-2-phenyl-3-(2,2,2-trifluoro-acetyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-carbamic acid tert-butyl ester (4.3 g, 11.5 mmol) and methylene chloride (75 mL) was immersed in a 0° C. bath, trifluoroacetic acid (8.0 mL, 103 mmol) was added dropwise, and the reaction stirred at 0° C. for 5 minutes then allowed to warm to room temperature and stir for 5 hours. The solvent was removed at reduced pressure and the material dried in vacuo to give the title compound as a trifluoroacetic acid salt. (quantitative yield).

Workup

  1. customwas immersed in a 0° C.
  2. temperatureto warm to room temperature
  3. stirringstir for 5 hours
  4. customThe solvent was removed at reduced pressure
  5. customthe material dried in vacuo

Sources & evidence

ORD record
ord-3feda96a41554287af8b69d41e89f6db
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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