Hydrochloric Acid → HCID 23387363, compound

HRID 1790780Notes

Reaction equation

HRID 1790780 reaction equation
C([CH:5]([O:10][C:11](=[O:27])[C@H:12]([CH:24]([CH3:26])[CH3:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:6][C:7]([O-:9])=[O:8])=CCC.[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(O)[O-].[Na+].Cl>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:17]([O:16][C:14]([NH:13][C@H:12]([C:11]([O:10][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:27])[CH:24]([CH3:26])[CH3:25])=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 86585845HCID 86585845, compound

Product 1

HCID 23387363HCID 23387363, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of 3-buten-1-yl-3-(N-benzyloxycarbonyl-L-valyloxy)-propionate (9.2 g, 30 mmole) in 150 ml benzene was added tetrabutylammonium bromide (1.62 g, 5 mmole) and 100 ml water. The mixture was cooled to about 5° C. and potassium permanganate (14.82 g, 90 mmole) was added in portions. The mixture was stirred 2 hours at room temperature, diluted with water and decolorized by the addition of sodium bisulfite. The mixture was acidified with 2M hydrogen chloride and extracted 3 times with ethyl acetate. The combined organic phases were washed with water and dried with sodium sulfate. The solution was evaporated under reduced pressure and the product isolated by silica gel column chromatography with hexane/ethyl acetate. Yield: 5.4 g=55%. The compound can be activated and esterified to a drug or further modified as described below.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried with sodium sulfate
  4. customThe solution was evaporated under reduced pressure
  5. customthe product isolated by silica gel column chromatography with hexane/ethyl acetate

Sources & evidence

ORD record
ord-bcc8e27aeab242b28597087af1c81f63
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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