HCID 10372347, compound → HCID 53796332, compound

HRID 1194982Notes

Reaction equation

HRID 1194982 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:27][C@H:28]([C:30]([N:32]2[C@H:39]([C:40]([O:42]CC3C=CC=CC=3)=[O:41])[CH2:38][C@H:37]3[C@@H:33]2[CH2:34][CH2:35][CH2:36]3)=[O:31])[CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:27][C@H:28]([C:30]([N:32]2[C@H:39]([C:40]([OH:42])=[O:41])[CH2:38][C@H:37]3[C@@H:33]2[CH2:34][CH2:35][CH2:36]3)=[O:31])[CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 10372347HCID 10372347, compound

Product 1

HCID 53796332HCID 53796332, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 50 ml of ethanol is dissolved 0.26 g of benzyl (S,S,S)-2-[N-[(S)-5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]-L-alanyl]-2-azabicyclo[3,3,0]octane-3-carboxylate, and a catalytic reduction is carried out at ambient temperature and under atmospheric pressure using 0.2 g of 10% palladium-carbon (50% wet) as a catalyst. After the reaction is allowed to proceed for 4 hours, the catalyst is filtered off, and the filtrate is concentrated under reduced pressure to give (S,S,S)-2-[N-[(S)-5-(4-piperidyl)-1-ethoxycarbonylpentyl]-L-alanyl]-2-azabicyclo[3,3,0]octane-3-carboxylic acid as a colorless oil. This product is dissolved in 5 ml of 1N aqueous sodium hydroxide, and the solution is allowed to stand at room temperature for 1 hour, made weakly acidic with 1 ml of acetic acid and purified by XAD-2 column chromatoraphy (0.15M aqueous ammonia-5% acetonitrile). The effluent is concentrated under reduced pressure, and the concentrate is lyophilized to give 0.15 g of (S,S,S)-2-[N-[(S)-5-(4-piperidyl)-1-carboxypentyl]-L-alanyl]-2-azabicyclo[3,3,0]octane-3-carboxylic acid as a colorless powder.

Workup

  1. customis carried out at ambient temperature and under atmospheric pressure
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a7127773ce6243098e4ebb712c0c516d
Source dataset
uspto-grants-1989_03
Patent number
US04816466

Reaction notes

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