Triethylamine → methyl-(R)-2-methanesulfonyloxybutyrate

HRID 2197658Notes

Reaction equation

HRID 2197658 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8](=[O:13])[C@H:9]([OH:12])[CH2:10][CH3:11].C(N(CC)CC)C.CC1CCCCC1.C(OCC)(=O)C>ClCCl.O>[CH3:6][O:7][C:8](=[O:13])[C@H:9]([O:12][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11701033(R)-Methyl 2-hydroxybutanoateHCID 66985183Ethyl acetate methylcyclohexane

Product 1

HCID 86617529methyl-(R)-2-methanesulfonyloxybutyrateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methanesulfonic acid chloride (5.33 g, 46.5 mmol, 1.1 equiv.) in dichloromethane (50 ml, 11 vol.) cooled to 0-5° C. is added over a period of 30 min. a mixture of methyl-(R)-2-hydroxybutyrate (5.1 g, 43.2 mmol, 1 equiv.) and triethylamine (4.7 g, 46.5 mmol, 1.1 equiv.) in dichloromethane (25 ml). When conversion is complete (TLC: methylcyclohexane/ethyl acetate=1/1 (v/v), dying with molybdatophosphoric acid; Rf=0.5), the mixture is allowed to warm to room temperature and 50 ml of water is added. The two resulting layers are separated and the organic layer is washed with 50 ml of water. The organic layer is dried over sodium carbonate and concentrated under reduced pressure to afford methyl-(R)-2-methanesulfonyloxybutyrate (IIg) as yellow oil (8.5 g, 43.2 mmol, 100%)

Workup

  1. additionis added over a period of 30 min.
  2. customThe two resulting layers are separated
  3. washthe organic layer is washed with 50 ml of water
  4. dry with materialThe organic layer is dried over sodium carbonate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bac517aa78d14803a1a44bd304f3ded4
Source dataset
uspto-grants-2012_12
Patent number
US08338621B2

Reaction notes

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