Acetonitrile → HCID 15867817, compound

HRID 1604121Notes

Reaction equation

HRID 1604121 reaction equation
C(#N)C.N1C=CC=CC=1.F.[O:11]([C@H:19]1[C@H:33](/[CH:34]=[CH:35]/[C@@H:36]([O:44][Si](C(C)(C)C)(C)C)[CH2:37][C@H:38]([CH3:43])[CH2:39][CH2:40][CH2:41][CH3:42])[C:22]([S:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:21][CH2:20]1)[Si](C(C)(C)C)(C)C>N1C=CC=CC=1>[OH:11][C@H:19]1[C@H:33](/[CH:34]=[CH:35]/[C@@H:36]([OH:44])[CH2:37][C@H:38]([CH3:43])[CH2:39][CH2:40][CH2:41][CH3:42])[C:22]([S:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:21][CH2:20]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 64774Pyridine, hydrofluoride (1:1)HCID 15867816HCID 15867816, compound

Product 1

HCID 15867817HCID 15867817, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of ice-cooled acetonitrile (1.5 mL) and pyridine (0.15 mL) was added hydrogen fluoride-pyridine (0.15 mL). To this solution was added methyl (11R,12S,13E,15S,17R)-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (150 mg, 0.238 mmol) in pyridine (0.15 mL). The ice bath was removed and the solution was agitated for 15 hours, while returning it to room temperature. The reaction solution was poured into a mixture of ethyl acetate and saturated aqueous sodium hydrogencarbonate. The desired product was extracted from this mixed solution with ethyl acetate. The extract was washed with brine, then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, then was purified by silica gel column chromatography (40 to 50% ethyl acetate/hexane) to obtain methyl (11R,12S,13E,15S,17R)-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (82 mg, 86%).

Workup

  1. customThe ice bath was removed
  2. customto room temperature
  3. additionThe reaction solution was poured into a mixture of ethyl acetate and saturated aqueous sodium hydrogencarbonate
  4. extractionThe desired product was extracted from this mixed solution with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe solution was concentrated under reduced pressure
  8. customwas purified by silica gel column chromatography (40 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2ad4cc8af94f4d96a33d623d71a2f264
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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