Acetic Acid → HCID 12802414, compound

HRID 1277385Notes

Reaction equation

HRID 1277385 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][NH2:37])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[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.[Pd]>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][NH2:37])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12802412HCID 12802412, compound

Product 1

HCID 12802414HCID 12802414, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In 50 ml of MeOH is dissolved 350 mg of Z-Tyr-(D)-Leu-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 concentrated and the residue is dissolved in a small amount of 1N-aqueous acetic acid and 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 320 through 340 ml are collected and lyophilized. 210 mg (60%); [α]D22 +22.6° (c=0.38, MeOH); Rf2 =0.34; amino acid analysis (acid hydrolyzate): Gly, 1.00, Leu, 1.00; Tyr, 0.90; Phe, 1.02; mean recovery rate 70%.

Workup

  1. concentrationthe filtrate is concentrated
  2. dissolutionthe residue is dissolved in a small amount of 1N-aqueous acetic acid
  3. washElution
  4. customare collected

Sources & evidence

ORD record
ord-a9ad49f8e3684caeb8dcc52dfa8630a6
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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