Trifluoroacetic acid → (2S,3S)-N-(4-acetyl-thiazol-2-yl)-2-[(R)-2-amino-2-(4-methoxy-phenyl)-acetylamino]-3-phenyl-butyramide

HRID 32808Notes

Reaction equation

HRID 32808 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:17](=[O:39])[NH:18][C@H:19]([C:28](=[O:38])[NH:29][C:30]1[S:31][CH:32]=[C:33]([C:35](=[O:37])[CH3:36])[N:34]=1)[C@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:35]([C:33]1[N:34]=[C:30]([NH:29][C:28](=[O:38])[C@@H:19]([NH:18][C:17](=[O:39])[C@H:8]([NH2:7])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C@H:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH3:21])[S:31][CH:32]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86603381[(R)-[(1S,2S)-1-(4-Acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propylcarbamoyl]-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester

Product 1

HCID 86603380(2S,3S)-N-(4-acetyl-thiazol-2-yl)-2-[(R)-2-amino-2-(4-methoxy-phenyl)-acetylamino]-3-phenyl-butyramideYield 111.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(R)-[(1S,2S)-1-(4-Acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propylcarbamoyl]-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester (3.1 g, 5.2 mmol) was stirred in dichloromethane (50 mL) in an ice-bath. Trifluoroacetic acid (50 mL) was added and the solution was stirred for 1 hour. The reaction mixture was evaporated and the residue was precipitated with hexanes/ether. The mixture was stirred vigorously for 10 minutes and then filtered. The solid was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic extracts were washed with brine and dried (sodium sulfate). Evaporation of the solvents gave (2S,3S)-N-(4-acetyl-thiazol-2-yl)-2-[(R)-2-amino-2-(4-methoxy-phenyl)-acetylamino]-3-phenyl-butyramide (2.7 g, 90% pure) as a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was precipitated with hexanes/ether
  3. stirringThe mixture was stirred vigorously for 10 minutes
  4. filtrationfiltered
  5. customThe solid was partitioned between aqueous sodium bicarbonate and dichloromethane
  6. customThe organic layer was separated
  7. extractionthe aqueous layer extracted with dichloromethane
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried (sodium sulfate)
  10. customEvaporation of the solvents

Sources & evidence

ORD record
ord-d94352266e364b5580633bdcc3407b78
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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