Hydrochloric Acid → H-Ile-Phe-OBut.HCl

HRID 904957Notes

Reaction equation

HRID 904957 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[ClH:35]>CO>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[ClH:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713277Z-Ile-Phe-OBut

Product 1

HCID 131713278H-Ile-Phe-OBut.HCl

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.65 g of Z-Ile-Phe-OBut are dissolved in 100 ml of methanol and subjected to catalytic hydrogenation at pH 4.5 after adding Pd-on-BaSO4 and 2 N methanolic hydrochloric acid. After the reaction is complete the catalyst is filtered off and the filtrate is concentrated. The residue crystallizes on being triturated with ether. Yield 2.57 g, melting point 107°-109°, [α]D24 =+15.9° (c=1, in methanol).

Workup

  1. filtrationis filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue crystallizes
  4. customon being triturated with ether
  5. customYield 2.57 g, melting point 107°-109°, [α]D24 =+15.9° (c=1, in methanol)

Sources & evidence

ORD record
ord-9453a1b03d424dd996eb03e0039f30e6
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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