(Diethylamino)sulfur trifluoride → HCID 70229943, compound

HRID 1976203Notes

Reaction equation

HRID 1976203 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH3:10][O:11][C:12](=[O:49])[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:34]C2CCCCO2)[C:27]([CH3:33])([CH3:32])[CH2:28][CH2:29][CH2:30][CH3:31])[C@H:22]([O:41]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:49])[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:34])[C:27]([CH3:33])([CH3:32])[CH2:28][CH2:29][CH2:30][CH3:31])[C@H:22]([OH:41])[CH2:21][C@H:20]1[F:7]

Participants

6

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 70226769HCID 70226769, 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-dimethyl-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-070e7a9e2c7646698049a4f8608cef76
Source dataset
uspto-grants-2001_05
Patent number
US06225347B1

Reaction notes

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