Acetic Acid → 3,5-Dioxohexanoic acid

HRID 893051Notes

Reaction equation

HRID 893051 reaction equation
ClC([O:4][CH2:5][CH:6](C)C)=O.CN1[CH2:15][CH2:14][O:13]CC1.C(OC(N[C@H](C(N[C@H](C(NCC(N)=O)=O)CC1N=CNC=1)=O)CCCCNC(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.N[C@H](C(N[C@H](C(NCC(N)=O)=O)CC1N=CNC=1)=O)CCCCN.[C:84]([OH:87])(=[O:86])[CH3:85]>O1CCCC1.[Pd].O>[CH3:6][C:5]([CH2:15][C:14]([CH2:85][C:84]([OH:87])=[O:86])=[O:13])=[O:4]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 178510999HCID 178510999, compoundHCID 178514039HCID 178514039, compound

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product was dissolved in anhydrous methanolic hydrogen chloride (saturated at 0° C.) for 30 minutes, followed by removal of solvent under reduced pressure, forming Nim -benzyloxycarbonyl-L-histidyl-glycine amide. This was dissolved in tetrahydrofuran, and isobutyl chloroformate, N-methylmorpholine, and Nα,Nε -dibenzyloxycarbonyl-L-lysyl-L-histidyl-glycine amide (3 hours at -20° C., then 1 hour at ambient temperature). This product was then dissolved in glacial acetic acid and hydrogenated overnight in the presence of 10% Pd-C catalyst. The resultant L-lysyl-L-histidyl-glycine amide was lyophilized from water several times, then purified by liquid chromatography on a C-18 reverse-phase column to yield the desired tripeptide amide as a triacetate salt.

Workup

  1. custom3 hours
  2. customat -20° C.
  3. custom1 hour
  4. customat ambient temperature
  5. custompurified by liquid chromatography on a C-18 reverse-phase column

Sources & evidence

ORD record
ord-06ab4d23253f4af0bd0a81458e193a9f
Source dataset
uspto-grants-1992_06
Patent number
US05120831

Reaction notes

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