Acetic Acid → HCID 10026551, compound

HRID 1031810Notes

Reaction equation

HRID 1031810 reaction equation
Br.Br.C([O:5][C:6]([C@@H:8]([NH:19][C@H:20]([C:22]([N:24]1[C@H:33]([C:34]([OH:36])=[O:35])[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1)=[O:23])[CH3:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:7])C.C(O)(=O)C>[OH-].[Na+]>[C:6]([C@@H:8]([NH:19][C@H:20]([C:22]([N:24]1[C@H:33]([C:34]([OH:36])=[O:35])[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25]1)=[O:23])[CH3:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18631458HCID 18631458, compound

Product 1

HCID 10026551HCID 10026551, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 8 ml of 1N aqueous sodium hydroxide is dissolved 0.3 g of (S)-2-[N-[(S)-1-ethoxycarbonyl-5-(4-piperidyl)pentyl]-L-alanyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.dihydrobromide, and the solution is allowed to stand at room temperature for 1 hour. The reaction solution is made acidic with 1 ml of acetic acid, and then purified by Amberlite XAD-2 column chromatography (0.1M aqueous ammonia-5% acetonitrile). The effluent is concentrated under reduced pressure, and lyophilized to give 0.16 g of (S)-2-[N-[(S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid as a colorless powder.

Workup

  1. custompurified by Amberlite XAD-2 column chromatography (0.1M aqueous ammonia-5% acetonitrile)
  2. concentrationThe effluent is concentrated under reduced pressure

Sources & evidence

ORD record
ord-437aa0b38d424c2d97c0f58cc4833a52
Source dataset
uspto-grants-1990_09
Patent number
US04954625

Reaction notes

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