Methyl 2-oxo-4-phenylbutanoate → Ammonium Hydroxide

HRID 2226422Notes

Reaction equation

HRID 2226422 reaction equation
[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]

Participants

5

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-06e12bcbb9ce4dbf993556ae715611da
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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