Hydrochloric Acid → HCID 131713264, compound

HRID 904946Notes

Reaction equation

HRID 904946 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:26]([NH2:28])=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[ClH:39]>CO>[NH2:1][C@H:2]([C:12]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([C:26]([NH2:28])=[O:27])[CH:23]([CH3:24])[CH3:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:8])[CH3:10].[ClH:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12944624HCID 12944624, compound

Product 1

HCID 131713264HCID 131713264, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6 g of Z-Glu(OBut)-Val-Val-NH2 are suspended in 200 ml of methanol. After adding Pd-on-BaSO4 and 2 N methanolic hydrochloric acid, the mixture is subjected to catalytic hydrogenation at pH 4.5. When the reaction is complete, the catalyst is filtered off and the filtrate is concentrated. The residue crystallizes on being triturated with ether. Yield 4.8 g, melting point 211°-219°, [α]D23 =-18.7° (c=1, in methanol).

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue crystallizes
  4. customon being triturated with ether
  5. customYield 4.8 g, melting point 211°-219°, [α]D23 =-18.7° (c=1, in methanol)

Sources & evidence

ORD record
ord-e2a6213a86524eee93adf7246f79df0f
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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