HCID 131720793, compound → HCID 131720792, compound

HRID 482014Notes

Reaction equation

HRID 482014 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-b5bcb604c1774276b8c74c3bf643ccb1
Source dataset
uspto-grants-1998_08
Patent number
US05792786

Reaction notes

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