Acetic Acid → 3,5-Dioxohexanoic acid

HRID 1078793Notes

Reaction equation

HRID 1078793 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 trifiuoroacetic 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 tripepride 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 tripepride ester as its triacetate salt.

Workup

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

Sources & evidence

ORD record
ord-c07a0b1b23324bcbad2891bc6092f1f8
Source dataset
uspto-grants-1996_08
Patent number
US05550183

Reaction notes

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