Acetonitrile → HCID 15867815, compound

HRID 1604120Notes

Reaction equation

HRID 1604120 reaction equation
C(#N)C.N1C=CC=CC=1.F.[C:11]([C:14]1[CH2:28][C@@H:27]([O:29][Si](C(C)(C)C)(C)C)[C@H:26](/[CH:37]=[CH:38]/[C@@H:39]([O:47][Si](C(C)(C)C)(C)C)[CH2:40][C@H:41]([CH3:46])[CH2:42][CH2:43][CH2:44][CH3:45])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])(=[O:13])[CH3:12]>N1C=CC=CC=1>[C:11]([C:14]1[CH2:28][C@@H:27]([OH:29])[C@H:26](/[CH:37]=[CH:38]/[C@@H:39]([OH:47])[CH2:40][C@H:41]([CH3:46])[CH2:42][CH2:43][CH2:44][CH3:45])[C:15]=1[S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 64774Pyridine, hydrofluoride (1:1)HCID 15867814HCID 15867814, compound

Product 1

HCID 15867815HCID 15867815, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of ice-cooled acetonitrile (1 mL) and pyridine (0.1 mL) was added a hydrogen fluoride-pyridine solution (0.1 mL). To this solution was added methyl (11R,12S,13E,15S,17R)-9-acetyl-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (12 mg, 0.019 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 a saturated aqueous sodium hydrogencarbonate. The desired product was extracted from this mixed solution of ethyl acetate. The extract was washed with brine, then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, then subjected to thin layer chromatography for separation (ethyl acetate:hexane=3:1) to obtain methyl (11R,12S,13E,15S,17R)-9-acetyl-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (3.2 mg, 39%).

Workup

  1. customThe ice bath was removed
  2. customto room temperature
  3. additionThe reaction solution was poured into a mixture of ethyl acetate
  4. extractionThe desired product was extracted from this mixed solution of 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. customsubjected to thin layer chromatography for separation (ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-932c1385f7c24763978f7938b3bd610b
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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