Water → Methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl ester

HRID 1694954Notes

Reaction equation

HRID 1694954 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([C@H:12]1[O:16][C:15](=[O:17])[C@H:14]([CH3:18])[CH2:13]1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@@H:10]([O:11][S:27]([CH3:26])(=[O:29])=[O:28])[C@@H:12]1[CH2:13][C@@H:14]([CH3:18])[C:15](=[O:17])[O:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 45277063HCID 45277063, compound

Product 1

HCID 86636121Methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7.80 g of (3R,5S)-5-[(R)-2-benzyloxy-1-hydroxyethyl]-3-methyldihydrofuran-2-one obtained in Example (76c) (31.2 mmol) in methylene chloride (200 ml) was cooled in an ice bath. Then, 9.45 g of triethylamine (93.6 mmol) and 5.36 g of methanesulfonyl chloride (47.0 mmol) were added thereto, and the mixture was stirred at the same temperature for three hours. 500 ml of water was added to the reaction mixture, followed by extraction with methylene chloride. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=4/1-1/1) to obtain 9.90 g of the title compound (yield: 97%).

Workup

  1. extractionfollowed by extraction with methylene chloride
  2. washThen, the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=4/1-1/1)

Sources & evidence

ORD record
ord-49ea73aa251c4edab06c136a9b47974e
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

Loading…