Hydrochloric Acid → H-Val-Tyr(But)-OBut.HCl

HRID 904962Notes

Reaction equation

HRID 904962 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:6]([NH:8][C@H:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:13][CH:12]=1)=[O:7])[CH:3]([CH3:5])[CH3:4].[ClH:39]>CO.[H][H]>[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[CH:15][CH:16]=1)=[O:7])[CH:3]([CH3:5])[CH3:4].[ClH:39]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 131713283Z-Val-Tyr(But)-OBut

Product 1

HCID 131713284H-Val-Tyr(But)-OBut.HCl

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Pd-on-charcoal catalyst is added to a solution of 31 g (58.8 mmoles) of Z-Val-Tyr(But)-OBut in 300 ml of methanol and hydrogen is passed through the solution at pH 4.5 (autotitrator) while stirring and adding approx. 2 N methanolic hydrochloric acid, until no further methanolic hydrochloric acid is taken up. The catalyst is then filtered off and the filtrate is concentrated. The residue is triturated with ether, filtered off and dried. Yield 23.6 g (94%), melting point 159°-161°, [α]D20 =+19.4° (c=1, methanol).

Workup

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is triturated with ether
  4. filtrationfiltered off
  5. customdried
  6. customYield 23.6 g (94%), melting point 159°-161°, [α]D20 =+19.4° (c=1, methanol)

Sources & evidence

ORD record
ord-eb138c4726194b2ca83c63f36bbff852
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

Loading…