Acetic Acid → HCID 12802420, compound

HRID 1277387Notes

Reaction equation

HRID 1277387 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][NH2:34])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(O)(=O)C>CO.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[Pd]>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][NH2:34])=[O:32])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 12802418HCID 12802418, compound

Product 1

HCID 12802420HCID 12802420, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

In 50 ml of MeOH is dissolved 250 mg of Z-Tyr-(D)-Ala-Gly-Phe-NH-NH2, and following addition of 0.1 ml of acetic acid, catalytic reduction is carried out with palladium black as the catalyst. The catalyst is filteredoff, the filtrate is dissolved in a small amount of 1 N-aqueous acetic acidand the solution is put on a column of Sephadex LH-20(2.5×120 cm). Elution is carried out with 1 N-aqueous acetic acid and fractions from 310ml through 335 ml are pooled and lyophilized. 95 mg (38%); [α]D22 +20.5° (c=0.2, MeOH); Rf2 =0.22; amino acid analysis (hydrolyzed with HCl): Gly, 1.00; Ala, 1.05; Tyr, 0.89; Phe,1.01; mean recovery rate 81%.

Workup

  1. washElution

Sources & evidence

ORD record
ord-eb01311755f4442dbc4e8262a334c04e
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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