Acetonitrile → HCID 15867800, compound

HRID 1604111Notes

Reaction equation

HRID 1604111 reaction equation
C(#N)C.N1C=CC=CC=1.F.[CH2:11]([C:16]1[CH2:30][C@@H:29]([O:31][Si](C(C)(C)C)(C)C)[C@H:28](/[CH:39]=[CH:40]/[C@@H:41]([O:49][Si](C(C)(C)C)(C)C)[CH2:42][C@H:43]([CH3:48])[CH2:44][CH2:45][CH2:46][CH3:47])[C:17]=1[S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:12][CH2:13][CH2:14][CH3:15]>N1C=CC=CC=1>[CH2:11]([C:16]1[CH2:30][C@@H:29]([OH:31])[C@H:28](/[CH:39]=[CH:40]/[C@@H:41]([OH:49])[CH2:42][C@H:43]([CH3:48])[CH2:44][CH2:45][CH2:46][CH3:47])[C:17]=1[S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 64774Pyridine, hydrofluoride (1:1)HCID 15867799HCID 15867799, compound

Product 1

HCID 15867800HCID 15867800, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of ice-cooled acetonitrile (1 mL) and pyridine (0.1 mL) was added hydrogen fluoride-pyridine (0.1 mL). To this solution was added methyl (11R,12S,13E,15S,17R)-9-pentyl-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (71 mg, 0.10 mmol) in pyridine (0.1 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 chromotography (30 to 50% ethyl acetate/hexane) to obtain methyl (11R,12S,13E,15S,17R)-9-pentyl-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (24 mg, 50%).

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 chromotography (30 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f36caeca4cf14edcb6df3859e527549c
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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