(3S)-4-[4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl]-3-[([3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)amino]butyl dimethyl phosphate → (3S)-4-[4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl]-3-[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)amino]butyl dihydrogen phosphate

HRID 1785052

반응식

HRID 1785052 반응식
[P:1]([O:39]C)([O:37]C)([O:3][CH2:4][CH2:5][C@@H:6]([NH:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[C:28]([Cl:36])[CH:27]=1)=[O:25])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([C:20](=[O:22])[CH3:21])[N:17]([CH3:19])[CH:18]=2)=[CH:10][CH:9]=1)=[O:2]>Br.CC(O)=O>[P:1]([OH:37])([OH:39])([O:3][CH2:4][CH2:5][C@@H:6]([NH:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[C:28]([Cl:36])[CH:27]=1)=[O:25])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([C:20](=[O:22])[CH3:21])[N:17]([CH3:19])[CH:18]=2)=[CH:10][CH:9]=1)=[O:2]

참가 물질

4

반응물 1

HCID 57594157(3S)-4-[4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl]-3-[([3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)amino]butyl dimethyl phosphate

생성물 1

HCID 16723062(3S)-4-[4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl]-3-[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)amino]butyl dihydrogen phosphate수율 19%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 260Hydrogen Bromide용매

반응 조건

온도
60 °C

실험 절차

A yellow solution of (3S)-4-[4-(2-acetyl-1-methyl-1H-imidazol-4-yl)phenyl]-3-[({3-chloro-4-[(1-methylethyl)oxy]phenyl}carbonyl)amino]butyl dimethyl phosphate (475 mg, 0.804 mmol) in 30% HBr in AcOH was placed in a pre-heated (60° C.) bath for 10 min, then immediately allowed to cool to rt. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in DMSO (6 mL), filtered and purified by Gilson reverse phase HPLC (MeCN/H2O with 0.1% TFA). The MeCN of the clean fractions was removed under reduced pressure and the remaining aqueous solution was frozen and lyophilyzed overnight to give 84 mg (19%) of the title compound as a yellow powder. LC/MS (ES) m/e 564.2 (M+H)+.

후처리

  1. temperatureto cool to rt
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in DMSO (6 mL)
  4. filtrationfiltered
  5. custompurified by Gilson reverse phase HPLC (MeCN/H2O with 0.1% TFA)
  6. customThe MeCN of the clean fractions was removed under reduced pressure
  7. temperaturethe remaining aqueous solution was frozen

출처 및 근거

ORD 기록
ord-a364b73772ed4c06a987b41907701bd9
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504413B2

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