N-Benzyloxycarbonyl-D-alanyl-alpha-L-aspartyl-D-alanine isopropyl ester → D-Alanyl-alpha-L-aspartyl-D-alanine isopropyl ester

HRID 868651Notes

Reaction equation

HRID 868651 reaction equation
[CH:1]([O:4][C:5](=[O:32])[C@@H:6]([CH3:31])[NH:7][C:8](=[O:30])[C@H:9]([CH2:26][C:27](=[O:29])[OH:28])[NH:10][C:11](=[O:25])[C@@H:12]([CH3:24])[NH:13]C(OCC1C=CC=CC=1)=O)([CH3:3])[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[CH:1]([O:4][C:5](=[O:32])[C@@H:6]([CH3:31])[NH:7][C:8](=[O:30])[C@H:9]([CH2:26][C:27](=[O:28])[OH:29])[NH:10][C:11](=[O:25])[C@@H:12]([CH3:24])[NH2:13])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 22840270N-Benzyloxycarbonyl-D-alanyl-alpha-L-aspartyl-D-alanine isopropyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 14151478D-Alanyl-alpha-L-aspartyl-D-alanine isopropyl esterYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-Benzyloxycarbonyl-D-alanyl-α-L-aspartyl-D-alanine isopropyl ester (2.5 g) was dissolved in 100 ml of 80% aqueous acetic acid, and the solution was subjected to catalytic reduction in a hydrogen gas stream at room temperature for four hours using palladium/carbon as catalyst. After filtering off the catalyst, the filtrate was concentrated to dryness under reduced pressure, affording 1.6 g of white powder. M.p.: 219°-221° C.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-97fc7cdacb70457bb905db7d8b165010
Source dataset
uspto-grants-1988_10
Patent number
US04780528

Reaction notes

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