Sodium Hydroxide → Propanal

HRID 433092노트

반응식

HRID 433092 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]([C@@H:24]([CH3:36])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)[CH2:21][CH2:22][CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[BH4-].[OH-].[Na+]>O1CCCC1.C(O)(=O)C>[CH:12](=[O:15])[CH2:13][CH3:14].[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]([C@@H:24]([CH3:36])[CH2:25][C:26]2[CH:27]=[CH:28][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:30][CH:31]=2)[CH2:21][CH2:22][CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 587719034-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

생성물 2

HCID 527PropanalHCID 587719034-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매2회

실험 절차

4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester A mixture of sodium borohydride (0.55 g) and tetrahydrofuran (40 ml) was stirred and a mixture of acetic acid (2.62 g) and tetrohydrofuran (10 ml) slowly added with cooling to maintain the temperature below ambient. The mixture was stirred for several hours. A solution of the 4-{4-[2-(4-methanesulfonyl-phenyl)-1-methyl-ethylamino]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (7.0 g) and propionaldehyde (0.85 g) in tetrahydrofuran (25 ml) was prepared. The solution was slowly added to the borohydride mixture with stirring. The mixture stirred several hours followed by slow addition of 25% sodium hydroxide solution (14 g).The upper organic layer was distilled under vacuum. The residue was dissolved in toluene and washed with water. The organic layer vacuum distilled to yield 7.5g of 4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester as an oil.

후처리

  1. additionslowly added
  2. temperaturewith cooling
  3. temperatureto maintain the temperature below ambient
  4. stirringThe mixture was stirred for several hours
  5. stirringwith stirring
  6. stirringThe mixture stirred several hours
  7. distillationwas distilled under vacuum
  8. dissolutionThe residue was dissolved in toluene
  9. washwashed with water
  10. distillationThe organic layer vacuum distilled

출처 및 근거

ORD 기록
ord-65356eaef3464cc38eb0f2357e09dac0
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667301B2

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