HCID 131720793, compound → HCID 131720792, compound

HRID 276143Notes

Reaction equation

HRID 276143 reaction equation
N(C(OCC1C=CC=CC=1)=O)CC(O)=O.[CH2:16]([OH:23])[C:17]([NH2:22])([CH2:20][OH:21])[CH2:18][OH:19].[NH:24](C(OCC1C=CC=CC=1)=O)[C@H:25]([C:27]([OH:29])=[O:28])[CH3:26].C(O)C(N)(CO)CO>>[NH2:24][C@H:25]([C:27]([OH:29])=[O:28])[CH3:26].[CH2:16]([OH:23])[C:17]([NH2:22])([CH2:20][OH:21])[CH2:18][OH:19]

Participants

3

Reactant 2

HCID 131720793HCID 131720793, compoundHCID 131720794HCID 131720794, compound

Product 1

HCID 131720792HCID 131720792, compound

Procedure

The title compound was obtained in quantitative yield by hydrogenation of a solution of Z-Gly-Tris in ethanol at 40 atm. pressure in a Parr hydrogenator in the presence of palladium on carbon (10%). The removal of the benzyloxycarbonyl group was monitored by HPLC (System A). The catalyst was removed by filtration and washed with ethanol. Evaporation of the solvent gave the title product in 95% purity as shown by 1H NMR spectroscopy. Ala-Tris was prepared in an analogous manner. The preparation of Z-Gly-Tris and Z-Ala-Tris are described in Whittaker, R. G., Hayes, P. J., and Bender, V. J. (1993) Peptide Research 6, 125 and Australian Patent No. 649242.

Workup

  1. customThe removal of the benzyloxycarbonyl group
  2. customThe catalyst was removed by filtration
  3. washwashed with ethanol
  4. customEvaporation of the solvent
  5. customgave the title product in 95% purity

Sources & evidence

ORD record
ord-58d51112ecf044be94638b297d020765
Source dataset
uspto-grants-2002_03
Patent number
US06353124B1

Reaction notes

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