Z-Gly-Phe-NHNH-COCH3 → H-Gly-Phe-NHNH-COCH3

HRID 1277399Notes

Reaction equation

HRID 1277399 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][NH:17][C:18]([CH3:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]>[Pd].CO>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][NH:17][C:18]([CH3:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 1

HCID 12919697Z-Gly-Phe-NHNH-COCH3

Product 1

HCID 131712285H-Gly-Phe-NHNH-COCH3Yield 26.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Z-Gly-Phe-NHNH-COCH3 (5 g) is hydrogenated over a Pd-black as a catalyst in MeOH (100 ml). The catalyst is filtered and the filtrate is evaporated to give 3.5 g of H-Gly-Phe-NHNH-COCH3 as crystals, H-Gly-Phe-NHNH-COCH3 (0.89 g) and Z-(D)-Nva-ONB, which is prepared from Z-(D)-Nva-OH (0.80 g) and HONB (0.63 g) by the DCC method, are dissolved in DMF (10 ml). The mixture is stirred for 10 hr. at room temperature and evaporated. The residue is treated with diethylether to give a powder which is crystallized from acetonitrile; yield 1.3 g. m.p. 235°-237° C., [α]D23 +3.4° (c=0.45, DMF), Rf1 =0.44.

Workup

  1. filtrationThe catalyst is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-f8d78ef0f1ea43b0824acf41475499e7
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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