Hydrochloric Acid → HCID 23387363, compound

HRID 489026Notes

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

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

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

Sources & evidence

ORD record: ord-bc43e89d45e449abb88fb0509ff89e73
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974802B2

Reaction notes

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