Phenylpyruvic acid → Ammonium Hydroxide

HRID 2226389Notes

Reaction equation

HRID 2226389 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].[C:18]1([CH2:24][C:25](=O)[C:26]([OH:28])=[O:27])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>O.CO>[OH-:5].[NH4+:1].[C:26]([CH:25]([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])[CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([OH:28])=[O:27]

Participants

6

Reactant 3

HCID 997Phenylpyruvic acidHCID 5003444Sodium cyanoborohydrideHCID 13146116HCID 13146116, compound

Product 2

HCID 14923Ammonium HydroxideYield 14%HCID 67852421HCID 67852421, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a mixture of 1-[(S)-alanyl]octahydroindole-2(S)-carboxylic acid (prepared as described in Example 1) and phenylpyruvic acid in methanol water at a pH of about 7, at room temperature, add sodium cyanoborohydride. Upon completion of the reaction, absorb the residue on a XAD-2 resin and elute with methanol followed by further purification by elution from silica gel using chloroform:methanol: 14% ammonium hydroxide 1:1:1 to isolate the title compound.

Workup

  1. customUpon completion of the reaction
  2. customabsorb the residue on a XAD-2 resin
  3. washelute with methanol
  4. customfollowed by further purification by elution from silica gel

Sources & evidence

ORD record
ord-52cadb53b7504ba7b8068e44b611f4ce
Source dataset
uspto-grants-1994_09
Patent number
US05348944

Reaction notes

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