Hydrochloric Acid → H-Gln-Asp(OtBu)-Phe-OCH3.HCl

HRID 971543Notes

Reaction equation

HRID 971543 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:20]([NH:22][C@H:23]([C:31]([O:33][CH3:34])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])[CH2:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[H][H].[ClH:47].O1CCOCC1>[Pd]>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:20]([NH:22][C@H:23]([C:31]([O:33][CH3:34])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])[CH2:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[ClH:47]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131711562Z-Gln-Asp(OtBu)-Phe-OCH3HCID 178418361HCID 178418361, compound

Product 1

HCID 131711564H-Gln-Asp(OtBu)-Phe-OCH3.HCl

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4.4 g of Z-Gln-Asp(OtBu)-Phe-OCH3 are decarbobenzoxylated with hydrogen at room temperature in a duck-shaped shaking flask after adding 2.4 ml of hydrogen chloride in dioxane (3.0 N, 7.2 mmols) amd 900 mg of 10% strength palladium on charcoal catalyst. After completion of the hydrogen uptake the mixture is filtered and the filtrate evaporated to dryness in vacuo. The yellowish solid residue is twice triturated with ether and used for the next step without further purification.

Workup

  1. filtrationAfter completion of the hydrogen uptake the mixture is filtered
  2. customthe filtrate evaporated to dryness in vacuo
  3. customThe yellowish solid residue is twice triturated with ether
  4. customused for the next step without further purification

Sources & evidence

ORD record
ord-657ac75e38ed4a0cb02c50d20e3ad5aa
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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