Hydrochloric Acid → (S)-methyl 2-(methylsulfonyloxy)-2-phenylacetate

HRID 76964Notes

Reaction equation

HRID 76964 reaction equation
[OH:1][C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[S:13](Cl)([CH3:16])(=[O:15])=[O:14].Cl>C(Cl)Cl>[CH3:16][S:13]([O:1][C@@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 643570methyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 10999262(S)-methyl 2-(methylsulfonyloxy)-2-phenylacetateYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 2-hydroxy-2-phenylacetate (20.0 g, 120 mmol) in DCM (240 mL) maintained at 0° C. under N2 flowstream, are added mesylchloride (11.2 mL, 144 mmol) and TEA (20.1 mL, 144 mmol) and the mixture is stirred at RT for 1 hour (UPLC-MS monitoring: complete conversion). The mixture is cooled to 0° C., 0.1N HCl (240 mL) is added and the desired compound is extracted with DCM (2×200 mL). The combined DCM phases are dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by filtration through a silica bed eluting with DCM, obtaining 22.4 g of the title compound as white solid (76% yield).

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. extractionthe desired compound is extracted with DCM (2×200 mL)
  3. dry with materialThe combined DCM phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. filtrationThe resulting crude is purified by filtration through a silica bed
  7. washeluting with DCM

Sources & evidence

ORD record
ord-d73584fc7c0f4abbb56149e76fc79912
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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