Sodium Hydroxide → HCID 69592949, compound

HRID 1825250Notes

Reaction equation

HRID 1825250 reaction equation
C([O:8][C:9](=[O:34])[CH:10]([NH:15][CH:16]([C:30]([O:32]C)=[O:31])[CH2:17][C:18]1[CH:22]=[CH:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:19]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1.[OH-].[Na+]>CO>[CH2:23]([N:20]1[CH:21]=[CH:22][C:18]([CH2:17][C@H:16]([NH:15][C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:34])=[O:8])[C:30]([OH:32])=[O:31])=[N:19]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1.[CH2:23]([N:20]1[CH:21]=[CH:22][C:18]([CH2:17][C@@H:16]([NH:15][C@@H:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:9]([OH:34])=[O:8])[C:30]([OH:32])=[O:31])=[N:19]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69593160HCID 69593160, compound

Product 2

HCID 69592949HCID 69592949, compoundHCID 69593204HCID 69593204, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-(1-Benzylpyrazol-3-yl)-1-methoxycarbonyl-ethylamino]-4-methylpentanoic acid benzyl ester (150 mg, 0.324 mmol) was dissolved in 3 mL of MeOH and a 1.0 M solution of NaOH (3.24 mL, 3.24 mmol) was added. The reaction mixture was stirred for 14 h at room temperature and then concentrated to give a white solid. Purification by reverse-phase HPLC chromatography provided (S,S)-2-[2-(1-benzyl-1H-pyrazol-3-yl)-1-carboxy-ethylamino]-4-methyl pentanoic acid (less polar fractions, 52-6a, R=CH2Ph) and (S,R)-2-[2-(1-benzyl-1H-pyrazol-3-yl)-1-carboxy-ethylamino]-4-methyl pentanoic acid (more polar fractions, 52-6b, R=CH2Ph) as white powders.

Workup

  1. concentrationconcentrated
  2. customto give a white solid
  3. customPurification by reverse-phase HPLC chromatography

Sources & evidence

ORD record
ord-baf144285d664f849df4fdab1a5ec7a0
Source dataset
uspto-grants-2006_05
Patent number
US07045532B2

Reaction notes

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