HCID 131712674, compound → L-Asparaginyl-L-phenylalanyl-L-phenylalanine

HRID 1447396Notes

Reaction equation

HRID 1447396 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]>CO.O.[Pd]>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

5

Reactant 1

HCID 131712674HCID 131712674, compound

Product 1

HCID 22820605L-Asparaginyl-L-phenylalanyl-L-phenylalanine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 20.5 g of Z-Asn-Phe-Phe-OH (see case 4-11346, stage 1.5A) in 270 ml of methanol and 30 ml of water is hydrogenated at room temperature on 2 g of palladium-on-carbon (10%) for 4 hours. After filtering off the catalyst, the filtrate is concentrated by evaporation in vacuo and the residue is used directly in the next stage.

Workup

  1. filtrationAfter filtering off the catalyst
  2. concentrationthe filtrate is concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-f95ff296cf724b128294e1eedf01c16e
Source dataset
uspto-grants-1982_02
Patent number
US04316890

Reaction notes

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