Methanesulfonyl chloride → HCID 86650321, compound

HRID 451204Notes

Reaction equation

HRID 451204 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([N:12]1[CH2:16][C@@H:15]([OH:17])[CH2:14][O:13]1)=[O:11].C(N(CC)C(C)C)(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([N:12]1[CH2:16][C@@H:15]([O:17][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:14][O:13]1)=[O:11]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 6933978HCID 6933978, compound

Product 1

HCID 86650321HCID 86650321, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(R)-4-Hydroxyisoxazolidine-2-carbonyl]benzoic acid methyl ester (prepared by the method of Martin et al., Tetrahedron Lett., 2007, 47, 7635) (3.50 g, 14.0 mmol) was dissolved in dichloromethane (100 mL) and N,N-diisopropylethylamine (3.55 mL, 20.3 mmol), then methanesulfonyl chloride (1.40 mL, 18.5 mmol) was added and the mixture was stirred at room temperature for 18 hours. The mixture was washed with 0.1M HCl solution (100 mL), dried (Na2SO4) and concentrated in vacuo to give the title compound as a yellow oil (5.00 g, 100%). δH (DMSO-d6) 7.92-7.46 (4H, m), 4.28 (1H, m) 4.17-4.14 (2H, m), 4.06-3.92 (2H, m), 3.82 (3H, s), 3.31 (3H, s). LCMS (ES+) RT 1.45 minutes, 330 (M+H)+ (pH 3).

Workup

  1. washThe mixture was washed with 0.1M HCl solution (100 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b978e00c3c74fc3bb3decf83ed97dbf
Source dataset
uspto-grants-2013_07
Patent number
US08487101B2

Reaction notes

Loading…