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 471298ノート

反応式

HRID 471298 の反応式
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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-51802a343408453aa512091ec98cd908
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

読み込み中…