Acetic Acid → 3,5-Dioxohexanoic acid

HRID 893050Notes

Reaction equation

HRID 893050 reaction equation
[CH2:1]([O:8]C(NCC(O)=O)=O)[C:2]1C=CC=[CH:4][CH:3]=1.CN1CC[O:20]CC1.ClC(OCC(C)C)=O.[H][H].[C:33]([OH:36])(=[O:35])[CH3:34]>C1COCC1.[Pd]>[CH3:4][C:3]([CH2:2][C:1]([CH2:34][C:33]([OH:36])=[O:35])=[O:8])=[O:20]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 79724-MethylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 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 is treated with 1/1 trifluoroacetic acid/dichloromethane at room temperature, neutralized with saturated aqueous sodium bicarbonate solution, and extracted into ethyl acetate. Evaporation gives the partially deblocked dipeptide, which is redissolved in dry THF and added to a stirring solution of benzyloxycarbonylglycine, N-methylmorpholine, and isobutyl chloroformate in dry THF at -15° C. The formed, fully protected tripeptide ester is totally deblocked by treatment with hydrogen gas in glacial acetic acid at room temperature in the presence of Pd-C catalyst. Filtration, evaporation and purification on a microcrystalline cellulose column followed by lyophilization give the desired tripeptide ester as its triacetate salt.

Workup

  1. filtrationFiltration, evaporation and purification on a microcrystalline cellulose column

Sources & evidence

ORD record
ord-550372ef543644c3a7ed24d4ebbf25ee
Source dataset
uspto-grants-1992_06
Patent number
US05120831

Reaction notes

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