Hydrochloric Acid → HCID 131709984, compound

HRID 971556Notes

Reaction equation

HRID 971556 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].Cl.[H][H].[CH3:38]O>O1CCOCC1.[Pd]>[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:22]([O:24][CH3:38])=[O:23])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14186027HCID 14186027, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131709984HCID 131709984, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

48.6 g of Z-Asp(OtBu)-Phe-OCH 3 in 700 ml of methanol are decarbobenzoxylated in a duck-shaped flask at room temperature after adding 33.5 ml of 3 N hydrogen chloride in dioxane and 5 g of 10% strength palladium catalyst on charcoal. After the hydrogen uptake has ended the mixture is filtered and the filtrate evaporated. 38.7 g of a white foam are obtained. In a thin layer chromatogram on silica gel in chloroform-methanol (9:1) Rf = 0.60; in chloroform-acetone (1:1) Rf = 0.58; Rf102E = 0.42. The product is employed for the subsequent condensation without additional purification.

Workup

  1. filtrationis filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-9889980d52d74036be83c44fbef4dbd3
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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