Acetic Acid → HCID 10253690, compound

HRID 1194967Notes

Reaction equation

HRID 1194967 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 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-d2228ed0ba9f4e52b54696132393fa91
Source dataset
uspto-grants-1989_03
Patent number
US04816466

Reaction notes

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