Acetic Acid → HCID 10253690, compound

HRID 1031803Notes

Reaction equation

HRID 1031803 reaction equation
Br.Br.C([O:5][C:6]([C@@H:8]([NH:19][C@H:20]([C:22]([N:24]([CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)[CH2:25][C:26]([OH:28])=[O:27])=[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]([CH:29]1[CH2:30][C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:37]1)[CH2:25][C:26]([OH:28])=[O:27])=[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)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18631455HCID 18631455, compound

Product 1

HCID 10253690HCID 10253690, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 6 ml of 1N aqueous sodium hydroxide is dissolved 0.25 g of N-[N-[(S)-1-ethoxycarbonyl-5-(4-piperidyl)-pentyl]-L-alanyl]-N-(indan-2-yl)glycine.dihydrobromide, and the solution is allowed to stand at room temperature for 30 minutes. The reaction solution is made weakly acidic with acetic acid and purified by column chromatography on Amberlite XAD-2 (0.1M aqueous ammonia-5% acetonitrile). The effluent is concentrated under reduced pressure and lyophilized to give 0.11 g of N-[N-[(S)-1-carboxy-5-(4-piperidyl)pentyl]-L-alanyl]-N-(indan-2-yl)glycine as a colorless powder.

Workup

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

Sources & evidence

ORD record
ord-5af94f12ac874f4da0f7dbd830ae7680
Source dataset
uspto-grants-1990_09
Patent number
US04954625

Reaction notes

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