Acetic Acid → 3,5-Dioxohexanoic acid

HRID 892692Notes

Reaction equation

HRID 892692 reaction equation
CN1[CH2:7][CH2:6][O:5]CC1.ClC([O:11][CH2:12][CH:13](C)C)=O.[H][H].[C:18]([OH:21])(=[O:20])[CH3:19]>C1COCC1.[Pd]>[CH3:13][C:12]([CH2:7][C:6]([CH2:19][C:18]([OH:21])=[O:20])=[O:5])=[O:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178418361HCID 178418361, compound

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The resulting fully protected dipeptide ester was treated with 30% trifluoroacetic acid in dichloromethane at ambient temperature for 40 minutes, neutralized with saturated aqueous sodium bicarbonate solution, and extracted into ethyl acetate. Evaporation gave the partially deprotected dipeptide, which was redissolved in dry THF and added to a stirring solution of Na,Ne -dibenzyloxycarbonyl-L-lysine, N-methylmorpholine an isobutyl chloroformate in dry THF at -20° C. The formed, fully protected tripeptide ester was totally deprotected by treatment with hydrogen gas in glacial acetic acid at ambient temperature in the presence of 10% Pd-C catalyst. Filtration through a layer of Celite, lyophilization from water, and purification by liquid chromatography on a C-18 reverse-phase column gave the desired tripeptide ester as its triacetate salt.

Workup

  1. filtrationFiltration through a layer of Celite, lyophilization
  2. customfrom water, and purification by liquid chromatography on a C-18 reverse-phase column

Sources & evidence

ORD record
ord-451895ed5b99405587520ae06a4e50a1
Source dataset
uspto-grants-1992_06
Patent number
US05118665

Reaction notes

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