Methyl 2-oxo-4-phenylbutanoate → Ammonium Hydroxide

HRID 2226422ノート

反応式

HRID 2226422 の反応式
[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]

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-06e12bcbb9ce4dbf993556ae715611da
出典データセット
uspto-grants-1994_09
特許番号
US05348944

反応ノート

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