Trifluoroacetic acid → HCID 86604054, compound

HRID 2222975Notes

Reaction equation

HRID 2222975 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:30])[C@@H:12]([NH:22]C(OC(C)(C)C)=O)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[S:8][CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:30])[C@@H:12]([NH2:22])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]#[N:21])[S:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86604052HCID 86604052, compound

Product 1

HCID 86604054HCID 86604054, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(S)-2-tert-Butoxycarbonylamino-3-(2-cyano-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester (3.2 g, 7.4 mmol) was dissolved into dry dichloromethane (20 mL) and trifluoroacetic acid (25 mL, 325 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour. The mixture was concentrated to dryness. The residue was cooled in an ice bath, then neutralized with saturated aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate and concentrated to give crude 2-[(S)-2-amino-3-(2-cyano-phenyl)-propionylamino]-thiazole-4-carboxylic acid methyl ester as a pale yellow solid (2.1 g, 86%).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated to dryness
  3. temperatureThe residue was cooled in an ice bath
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-519dd4a16fd34eb3b70002f19f93ce39
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

Loading…