(Diethylamino)sulfur trifluoride → HCID 70229943, compound

HRID 442789Notes

Reaction equation

HRID 442789 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH3:10][O:11][C:12](=[O:51])[CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][C@@H:19]1[C@@H:23](/[CH:24]=[CH:25]/[C@@H:26]([O:36]C2CCCCO2)[C:27]([CH2:34]C)([CH2:32]C)[CH2:28][CH2:29][CH2:30][CH3:31])[C@H:22]([O:43]C2CCCCO2)[CH2:21][C@@H:20]1O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH3:10][O:11][C:12](=[O:51])[CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][C@@H:19]1[C@@H:23](/[CH:24]=[CH:25]/[C@@H:26]([OH:36])[C:27]([CH3:34])([CH3:32])[CH2:28][CH2:29][CH2:30][CH3:31])[C@H:22]([OH:43])[CH2:21][C@H:20]1[F:7]

Participants

6

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 67583129HCID 67583129, compound

Product 1

HCID 70229943HCID 70229943, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

0.56 ml of diethylaminosulfur trifluoride (DAST) is instilled in a solution of 2.05 g of (4Z,13E)-(9S,11R,15R)-9-hydroxy-16,16-diethyl-11,15-bis-(tetrahydropyran-2-yloxy)-4,13-prostadienoic acid methyl ester in 43 ml of methylene chloride and 1.1 ml of pyridine at -70° C. and stirred for 3.5 hours at -70° C. Then it is added to 200 ml of 5% sodium bicarbonate solution cooled to 0° C. and allowed to stir vigorously for 10 minutes. Then it is extracted several times with methylene chloride, the extract is washed with water, dried over MgSO4 and concentrated by evaporation in a vacuum. The residue is stirred for 24 hours at 20° C. with 60 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10), concentrated by evaporation in a vacuum after addition of toluene and the raw product is purified by chromatography on silica gel with toluene/0-10% isopropanol. 306 mg of the title compound is obtained as oil.

Workup

  1. temperaturecooled to 0° C.
  2. stirringto stir vigorously for 10 minutes
  3. extractionThen it is extracted several times with methylene chloride
  4. washthe extract is washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated by evaporation in a vacuum
  7. stirringThe residue is stirred for 24 hours at 20° C. with 60 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10)
  8. concentrationconcentrated by evaporation in a vacuum
  9. additionafter addition of toluene
  10. customthe raw product is purified by chromatography on silica gel with toluene/0-10% isopropanol

Sources & evidence

ORD record
ord-aebeab9973024102aba5e904e4dc52fd
Source dataset
uspto-grants-1999_04
Patent number
US05891910

Reaction notes

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