Water → (1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-((4-phenylbenzoyl)oxy)-2-oxabicyclo(3.3.0)octan-3-one

HRID 584879Notes

Reaction equation

HRID 584879 reaction equation
S(=O)(=O)=O.N1C=CC=CC=1.[OH:11][C@H:12]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)/[CH:13]=[CH:14]/[C@@H:15]1[C@@H:22]2[C@@H:18]([O:19][C:20](=[O:23])[CH2:21]2)[CH2:17][C@H:16]1[O:24][C:25](=[O:38])[C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1.C(N(CC)CC)C.O>CS(C)=O.ClCCl>[O:11]=[C:12]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)/[CH:13]=[CH:14]/[C@@H:15]1[C@@H:22]2[C@@H:18]([O:19][C:20](=[O:23])[CH2:21]2)[CH2:17][C@H:16]1[O:24][C:25](=[O:38])[C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 9982721rel-(3AR,4R,5R,6aS)-4-((R,E)-3-hydroxy-5-phenylpent-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate

Product 1

HCID 10005375(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-((4-phenylbenzoyl)oxy)-2-oxabicyclo(3.3.0)octan-3-oneYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of pyridine sulfur trioxide (0.32 g) in DMSO (3.5 mL) was added dropwise to a stirred solution of compound [6a] (0.30 g) and triethylamine (0.40 g) in dichloromethane (4 mL) at −5-0° C. The mixture was stirred at the same temperature for 1 hour (TLC monitoring) and poured into cold water (15 mL). The mixture was stirred for 10 min at 0-5° C. The organic layer was separated, the water layer was extracted with dichloromethane (3×5 mL). The combined organic layers were washed with brine (3×10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. A solution of the residue in methanol (1 mL) was cold to −10° C. and kept at the same temperature for 3 hours. The precipitated crystals were filtered, washed on filter with cold methanol (2×1 mL) and dried under reduced pressure to a constant weight to give 0.26 g (87% yield) of crystalline compound [4a] with 94% purity by HPLC.

Workup

  1. stirringThe mixture was stirred for 10 min at 0-5° C
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted with dichloromethane (3×5 mL)
  4. washThe combined organic layers were washed with brine (3×10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customwas cold to −10° C.
  9. waitkept at the same temperature for 3 hours
  10. filtrationThe precipitated crystals were filtered
  11. washwashed
  12. filtrationon filter with cold methanol (2×1 mL)
  13. customdried under reduced pressure to a constant weight

Sources & evidence

ORD record
ord-8d87676abb78484287d7ba1cb24081fb
Source dataset
uspto-grants-2005_08
Patent number
US06927300B2

Reaction notes

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