Sodium Hydroxide → (4R,5E)-4-tert-butoxycarbonylamino-7-oxo-8-(3,5-dimethylphenyl)oct-5-enoic acid ethyl ester

HRID 853836노트

반응식

HRID 853836 반응식
[H-].[Na+].[O:3]=[C:4]([CH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)[CH2:5]P(=O)(OC)OC.[C:21]([O:25][C:26]([NH:28][C@@H:29]([CH:37]=O)[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:27])([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+]>O1CCCC1.O.C(OC)(C)(C)C>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][CH2:30][C@@H:29]([NH:28][C:26]([O:25][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:27])/[CH:37]=[CH:5]/[C:4](=[O:3])[CH2:12][C:13]1[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH3:36]

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 57894011ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoateHCID 71389878Dimethyl [3-(3,5-dimethylphenyl)-2-oxopropyl]phosphonate

생성물 1

HCID 69238228(4R,5E)-4-tert-butoxycarbonylamino-7-oxo-8-(3,5-dimethylphenyl)oct-5-enoic acid ethyl ester수율 64.7%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 15413tert-Butyl methyl ether용매

실험 절차

Under atmosphere of argon, a suspension of 60% sodium hydride (50 mg) was added by a solution of dimethyl (2-oxo-3-(3,5-dimethylphenyl)propyl)phosphonate (373 mg) in tetrahydrofuran (5 mL) at the temperature of 0° C. The mixture was stirred for an hour and then a solution of ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate (298 mg) in tetrahydrofuran (5 mL) was added to the mixture. The mixture was stirred for an hour. To the mixture, metyl tert-butyl ether and water were added, and then 1N a solution of sodium hydroxide was added. The organic layer was washed with saturated brine, dried over an anhydrous magnesium sulfate, concentrated and was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (300 mg) having the following physical data.

후처리

  1. stirringThe mixture was stirred for an hour
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over an anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customwas purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-e3560ee567e04209b146bba385980e9b
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256211B1

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