Methyl 2-oxo-4-phenylbutanoate → Ammonium Hydroxide

HRID 2226422노트

반응식

HRID 2226422 반응식
[NH2:1][C@H:2]([C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][CH:8]2[CH2:14][O:15][CH2:16][CH:7]12)=[O:5])[CH3:3].O=[C:18]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]([O:21][CH3:22])=[O:20]>CO>[OH-:5].[NH4+:1].[CH3:22][O:21][C:19]([CH:18]([NH:1][C@H:2]([C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][CH:8]2[CH2:14][O:15][CH2:16][CH:7]12)=[O:5])[CH3:3])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:20]

참가 물질

5

반응물 2

HCID 11805548Methyl 2-oxo-4-phenylbutanoateHCID 186548901-[(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

생성물 2

HCID 14923Ammonium Hydroxide수율 7%HCID 678524351-[N-(1-carbomethoxy-3-phenylpropyl)-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Dissolve 1-[(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid (prepared in paragraph C of this example) in absolute methanol. Add 2-oxo-4-phenylbutyric acid, methyl ester and 3 Angstrom molecular sieve pellets, and stir the resulting mixture at room temperature for eighteen hours. Filter the reaction mixture and treat the filtrate with sodium cyanoborohydride at room temperature for two hours. Concentrate the mixture under nitrogen and dilute the oil with dilute hydrochloric acid and stir at room temperature for one hour. Absorb the aqueous solution on XAD-2 (Rohm & Hass Co.) resin. Elute the resin with water and then with methanol. Concentrate the methanol solution and place the residue on a column of silica gel and elute with chloroform:isopropanol: 7% ammonium hydroxide 1:1:1 (organic layer) to give 1-[N-(1-methoxycarbonyl-3-phenylpropyl)-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)carboxylic acid.

후처리

  1. filtrationFilter the reaction mixture
  2. additiontreat the filtrate with sodium cyanoborohydride at room temperature for two hours
  3. concentrationConcentrate the mixture under nitrogen
  4. additiondilute the oil with dilute hydrochloric acid
  5. customAbsorb the aqueous solution on XAD-2 (Rohm & Hass Co.) resin
  6. washElute the resin with water
  7. concentrationConcentrate the methanol solution and place the residue on a column of silica gel
  8. washelute with chloroform

출처 및 근거

ORD 기록
ord-06e12bcbb9ce4dbf993556ae715611da
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05348944

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