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

HRID 1694990Notes

Reaction equation

HRID 1694990 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([C@H:12]1[O:16][C:15](=[O:17])[C@H:14]([CH2:18][CH3:19])[CH2:13]1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@@H:10]([O:11][S:28]([CH3:27])(=[O:30])=[O:29])[C@@H:12]1[CH2:13][C@@H:14]([CH2:18][CH3:19])[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 66645773(3R,5S)-5-[(R)-2-Benzyloxy-1-hydroxyethyl]-3-ethyldihydrofuran-2-one

Product 1

HCID 86636123Methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-4-ethyl-5-oxotetrahydrofuran-2-yl]ethyl esterYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 25.0 g of (3R,5S)-5-[(R)-2-benzyloxy-1-hydroxyethyl]-3-ethyldihydrofuran-2-one obtained in Example (106c) (94.7 mmol) in methylene chloride (600 ml) was cooled in an ice bath. Then, 28.7 g of triethylamine (284 mmol) and 15.9 g of methanesulfonyl chloride (139 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 31.2 g of the title compound (yield: 96%).

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-04d5ff15762d4f5b86e5df0647d134e7
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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