Ammonia → tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

HRID 471298노트

반응식

HRID 471298 반응식
C(OC([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]=[O:39])[CH:33]=2)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=O)(C)(C)C.N>CO>[Si:42]([O:41][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]=[O:39])[CH:33]=1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])([C:45]([CH3:46])([CH3:47])[CH3:48])([CH3:44])[CH3:43]

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 57989227tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

생성물 1

HCID 57989338tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate (Example 276, step h) (0.521 g) was suspended in methanol (20 mL) and treated with ‘880’ aqueous ammonia (2.5 mL) to give a suspension that was stirred at room temperature for 3 hours. The mixture was concentrated by blowing with a stream of nitrogen, and the residue was partitioned between ethyl acetate, water and brine, and the phases separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo to afford the subtitled compound. Yield 0.476 g. Material used immediately in the next step.

후처리

  1. customto give a suspension that
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate, water and brine
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-51802a343408453aa512091ec98cd908
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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