Ammonia → (R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde

HRID 471291노트

반응식

HRID 471291 반응식
C(=O)([O:7][C:8]1[CH:9]=[CH:10][C:11]([C@@H:19]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:20][NH:21][C:22]([CH3:33])([CH3:32])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[O:31])[CH:25]=2)=[C:12]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]=[CH:13]2)OC(C)(C)C.N>CO>[Si:35]([O:34][C@H:19]([C:11]1[CH:10]=[CH:9][C:8]([OH:7])=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15](=[O:18])[NH:16]2)[CH2:20][NH:21][C:22]([CH3:33])([CH3:32])[CH2:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[CH:30]=[O:31])([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36]

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 57989095(r)-Tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-formylphenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate

생성물 1

HCID 57989117(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of (R)-tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-formylphenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate (Example 275, step g) (0.42 g) in methanol (15 mL) was treated with ammonia (35% aqueous) (2 mL). The reaction mixture was allowed to stand for 3 hours at 20° C. The solvent was removed under a stream of nitrogen and the residue was partitioned between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate and the combined organics dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.34 g.

후처리

  1. customThe solvent was removed under a stream of nitrogen
  2. customthe residue was partitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organics dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d389c88e79bb442191acfb6daae39e4b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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