Z-Gly-Ala-Pro-OtBu → H-Gly-Ala-Pro-OtBu

HRID 1580898Notes

Reaction equation

HRID 1580898 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:8]([N:10]1[CH2:21][CH2:20][CH2:19][C@H:11]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:9])[CH3:7])=[O:4].[H][H]>CO.[Pd]>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([N:10]1[CH2:21][CH2:20][CH2:19][C@H:11]1[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[O:9])[CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 131709998Z-Gly-Ala-Pro-OtBuHCID 178418361HCID 178418361, compound

Product 1

HCID 131709997H-Gly-Ala-Pro-OtBu

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.06 g of Z-Gly-Ala-Pro-OtBu are hydrogenated in 30 ml of methanol in the presence of 300 mg of Pd on charcoal (10 %) at room temperature. The hydrogen uptake has ended after 90 minutes. The catalyst is filtered off and the filtrate is concentrated to about 5 ml. 10 ml of ether are added. The product crystallises out overnight. Melting point 132°-134°C; Rf = 0.3 in the system chloroform-methanol (1:1) on silica gel.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to about 5 ml
  3. addition10 ml of ether are added
  4. customThe product crystallises out overnight

Sources & evidence

ORD record
ord-6bc68e891ae1420cafa555e802c5512a
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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