Ethyl alpha-oxobenzenebutanoate → Ammonium Hydroxide

HRID 2226387Notes

Reaction equation

HRID 2226387 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][C@H:7]1[C:15]([OH:17])=[O:16])=[O:5])[CH3:3].O=[C:19]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:20]([O:22][CH2:23]C)=[O:21]>CO>[OH-:5].[NH4+:1].[CH3:23][O:22][C:20]([CH:19]([NH:1][C@H:2]([C:4]([N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][C@H:7]1[C:15]([OH:17])=[O:16])=[O:5])[CH3:3])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:21]

Participants

5

Reactant 2

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 13146116HCID 13146116, compound

Product 2

HCID 14923Ammonium HydroxideYield 7%HCID 67788181HCID 67788181, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1-[(S)-alanyl ]octahydroindole-2(S)-carboxylic acid (prepared in paragraph D of this example) in 100 ml of absolute methanol. Add 1.10 g 2-oxo-4-phenylbutyric acid, ethyl ester and 20 ml of 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 0.68 g 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 200 ml of a XAD-2 (Rohm & Haas-Co. resin). Elute the resin with 2000 ml of water and then with 2000 ml of methanol. Concentrate the methanol solution and place the residue on a column of silica gel (400 g, 60-200 mesh) and elute with chloroform:isopropanol: 7% ammonium hydroxide 1:1:1 (organic layer) to give 1-[N-(1-methoxycarbonyl-3-phenyl propyl)-(S)-alanyl]octahydroindole-2(S)-carboxylic acid, a white solid [ α]D26 -45.3° (ethanol), m.p. 71°-73°.

Workup

  1. filtrationFilter the reaction mixture
  2. additiontreat the filtrate with 0.68 g sodium cyanoborohydride at room temperature for two hours
  3. concentrationConcentrate the mixture under nitrogen
  4. additiondilute the oil with dilute hydrochloric acid
  5. stirringstir at room temperature for one hour
  6. customAbsorb the aqueous solution on 200 ml of a XAD-2 (Rohm & Haas-Co. resin)
  7. washElute the resin with 2000 ml of water
  8. concentrationConcentrate the methanol solution and place the residue on a column of silica gel (400 g, 60-200 mesh)
  9. washelute with chloroform

Sources & evidence

ORD record
ord-c2b1a86ea7614279aba6c39bba0f034c
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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