Methanesulfonyl chloride → Ethyl 3-cyclopropyl-2-[(methylsulphonyl)oxy]propanoate

HRID 56661Notes

Reaction equation

HRID 56661 reaction equation
C(N(C(C)C)C(C)C)C.[CH:10]1([CH2:13][CH:14]([OH:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11]1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH:10]1([CH2:13][CH:14]([O:20][S:22]([CH3:21])(=[O:24])=[O:23])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 116489250Ethyl 3-cyclopropyl-2-hydroxy-propanoate

Product 1

HCID 117605475Ethyl 3-cyclopropyl-2-[(methylsulphonyl)oxy]propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At RT, 2 ml (11.5 mmol, 2.4 eq.) of N-ethyl-N-(propan-2-yl)propan-2-amine were added to a solution of 1.9 g (purity 40%, 4.8 mmol) of ethyl 3-cyclopropyl-2-hydroxypropanoate (racemate) in 100 ml of dichloromethane, followed by the quick addition, at 0° C., of 0.45 ml (5.8 mmol, 1.2 eq.) of methanesulphonyl chloride. The reaction mixture was stirred at RT for 2 h and then quenched with ice. After phase separation, the organic phase was washed with three times with water and once with saturated sodium chloride solution. The combined organic phases were dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was used for the next step without further purification.

Workup

  1. customquenched with ice
  2. customAfter phase separation
  3. washthe organic phase was washed with three times with water and once with saturated sodium chloride solution
  4. dry with materialThe combined organic phases were dried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-3c4f11256fac413fa571551a72db8806
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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