Trifluoroacetic acid → Methyl 1,3-thiazole-4-carboxylate

HRID 2222966

반응식

HRID 2222966 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](NC(=O)[C@@H](NC(=O)C(NC(OC(C)(C)C)=O)C2C=CC(OCCOC)=CC=2)CC2C=CC=CC=2)[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]=[CH:7][S:8][CH:9]=1)=[O:4]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86604049HCID 86604049, 화합물

생성물 1

HCID 2773414Methyl 1,3-thiazole-4-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-((S)-2-{2-tert-Butoxycarbonylamino-2-[4-(2-methoxy-ethoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (a mixture of two epimers, R/S=85:15) (0.21 g, 0.343 mmol) was dissolved into dry dichloromethane (20 mL) and trifluoroacetic acid (2 mL, 26 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)-2A2-amino-2-[4-(2-methoxy-ethoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester as a white foam (a mixture of two epimers, R/S=85:15) (0.16 g, 91%).

후처리

  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

출처 및 근거

ORD 기록
ord-e1819b5a79f84755a4ffc697ef48f83a
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371869B2

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