Acetic Acid → tert-butyl (S)-4-((R)-1-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)-2,2-dimethylpropylamino)-1-methoxybutan-2-ylcarbamate

HRID 1028852노트

반응식

HRID 1028852 반응식
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[N:10]=[C:9]1[C@H:21]([NH2:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]([CH2:29][C@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:31][O:32][CH3:33])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])[N:10]=[C:9]1[C@H:21]([NH:26][CH2:27][CH2:29][C@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:31][O:32][CH3:33])[C:22]([CH3:23])([CH3:25])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 57805652(R)-1-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)-2,2-dimethylpropan-1-amineHCID 57976564tert-butyl (S)-1-formyl-3-methoxypropan-2-ylcarbamate

생성물 1

HCID 86602597tert-butyl (S)-4-((R)-1-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)-2,2-dimethylpropylamino)-1-methoxybutan-2-ylcarbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To (R)-1-(1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl)-2,2-dimethylpropan-1-amine (1 eq) in dichloromethane was added tert-butyl (S)-1-formyl-3-methoxypropan-2-ylcarbamate (1.5 eq) and acetic acid (1 eq). The reaction mixture was stirred at room temperature for 1 h. Sodium triacetoxy borohydride (2 eq) was added at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. Solvent was concentrated and crude was partitioned between ethyl acetate and satd. sodium bicarbonate. The organic layer was washed with water, brine and dried over sodium sulfate. Purification by silica gel chromatography (25% EtOAc/Hexane) provide pure product as a white foamy solid.

후처리

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred overnight
  3. concentrationSolvent was concentrated
  4. customcrude was partitioned between ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customPurification by silica gel chromatography (25% EtOAc/Hexane)
  8. customprovide pure product as a white foamy solid

출처 및 근거

ORD 기록
ord-b2e565d092e545fb9cf2a1d7c35034da
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735599B2

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