Trifluoroacetic acid → HCID 86603379, compound

HRID 32807Notes

Reaction equation

HRID 32807 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:17](=[O:27])[NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24](=[O:26])[CH3:25])[N:23]=1)[C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:24]([C:22]1[N:23]=[C:19]([NH:18][C:17](=[O:27])[C@@H:8]([NH2:7])[C@H:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[S:20][CH:21]=1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86603377[(1S,2S)-1-(4-acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 86603379HCID 86603379, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(1S,2S)-1-(4-Acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester (2.8 g, 6.25 mmol) was dissolved in dichloromethane (42 mL) in an ice bath. Trifluoroacetic acid (35 mL) was added. After 30 minutes, 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 was 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-amino-3-phenyl-butyramide (1.9 g, 95%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-76453ecf84534e8e8113ad4d090c92a9
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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