Dichloromethane → (R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 132440노트

반응식

HRID 132440 반응식
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22]C(OC(C)(C)C)=O)=[C:18]([CH3:30])[C:17]=1[CH2:31][O:32][C:33](=[O:35])[CH3:34])[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.FC(F)(F)C(O)=O>>[C:1]([O:9][C@H:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:30])[C:17]=1[CH2:31][O:32][C:33](=[O:35])[CH3:34])[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59732072(R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

생성물 1

HCID 59732065(R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate수율 97%

실험 절차

(R)-3-(2-(acetoxymethyl)-4-(tert-butoxycarbonylamino)-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate (19.5 g, 40.2 mmol) in dichloromethane (100.00 ml, 1554 mmol) was added trifluoroacetic acid (30.00 ml, 389 mmol). The reaction mixture was stirred at RT. After 4 h, LC-MS suggested complete removal of protecting group. The solvent was removed and the crude product was dissolved in dichloromethane (300 mL) and washed with aqueous NaHCO3. The solvent was removed to give (R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate (15.0 g, 38.9 mmol, 97% yield). MS (ESI) 408 (M+H); Rf=1.69.

후처리

  1. customremoval
  2. customThe solvent was removed
  3. dissolutionthe crude product was dissolved in dichloromethane (300 mL)
  4. washwashed with aqueous NaHCO3
  5. customThe solvent was removed

출처 및 근거

ORD 기록
ord-2092cad740ea4013ba9f93d43878e28b
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384931B2

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