Acetonitrile → HCID 12816582, compound

HRID 428821Notes

Reaction equation

HRID 428821 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH2:17][C:18]([OH:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:13]([O:25][Si](C(C)(C)C)(C)C)[CH2:12][C:11]1=[O:33].C(#N)C.F>O>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH2:17][C:18]([OH:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:13]([OH:25])[CH2:12][C:11]1=[O:33]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14917Hydrofluoric AcidHCID 131722977HCID 131722977, compound

Product 1

HCID 12816582HCID 12816582, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a Teflon container were placed (±)-methyl(16RS, 13E)-11-tert-butyldimethylsilyloxy-16-hydroxy-16-methyl-9-oxoprost-13-en-1-oate (1.89 g, 3.81 mmol) and acetonitrile (50 ml), whereby 46% hydrofluoric acid (4.5 ml) was added and stirred at room temperature for 2 h. The reaction mixture was added with water (120 ml) and extracted with methylene chloride (60 ml) two times. The combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate, a saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to remove solvent. The residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)] to give 1.44 g (99% yield) of Misoprostol;

Workup

  1. additionwas added
  2. extractionextracted with methylene chloride (60 ml) two times
  3. washThe combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate
  4. dry with materiala saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto remove solvent
  7. customThe residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)]

Sources & evidence

ORD record
ord-5635780cd49b4888a999365eb8dceca2
Source dataset
uspto-grants-2001_11
Patent number
US06313341B1

Reaction notes

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