Trifluoroacetic acid → HCID 86602062, compound

HRID 1295379Notes

Reaction equation

HRID 1295379 reaction equation
C(O[C:6](=O)[N:7]([C@@:9]12[CH2:14][CH:13]1[CH2:12][N:11]([C:15](=[O:34])[N:16]([C@H:18]([C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=1)[CH3:19])[CH3:17])[C@H:10]2[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:28][C:26]([F:27])([F:29])[C:24]1[CH:25]=[C:20]([C@@H:18]([N:16]([CH3:17])[C:15]([N:11]2[CH2:12][CH:13]3[C@@:9]([NH:7][CH3:6])([CH2:14]3)[C@@H:10]2[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:34])[CH3:19])[CH:21]=[C:22]([C:30]([F:31])([F:32])[F:33])[CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86602063HCID 86602063, compound

Product 1

HCID 86602062HCID 86602062, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask containing Intermediate 50, a mixture of four isomers, one being ((1S,2S)-3-{[(S)-1-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methyl-carbamoyl}-2-phenyl-3-aza-bicyclo[3.1.0]hex-1-yl)-methyl-carbamic acid tert-butyl ester (0.17 g, 0.30 mmol), and methylene chloride (5 mL) was immersed in a 0° C. bath. Trifluoroacetic acid (0.46 mL, 6.0 mmol) was added, and the reaction stirred for 16 hours at room temperature. The solvent was removed at reduced pressure and the residue partitioned between saturated sodium bicarbonate solution and methylene chloride, the organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound as an oil (0.15 g, quantitative yield).

Workup

  1. customwas immersed in a 0° C.
  2. customThe solvent was removed at reduced pressure
  3. customthe residue partitioned between saturated sodium bicarbonate solution and methylene chloride
  4. washthe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3709628cb19b4cfa9ea8850f6d994246
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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