Methanesulfonyl chloride → 2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl methanesulfonate

HRID 916809Notes

Reaction equation

[CH3:1][C:2]1([CH3:30])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[N:14]([CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][OH:29])=[CH:22][CH:21]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.C(N(C(C)C)CC)(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:40][S:41]([O:29][CH2:28][CH2:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][N:14]2[CH2:13][C@@H:12]([C:10]3[CH:9]=[CH:8][C:6]4[O:7][C:2]([CH3:30])([CH3:1])[O:3][CH2:4][C:5]=4[CH:11]=3)[O:16][C:15]2=[O:17])=[CH:25][CH:24]=1)(=[O:43])=[O:42]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{2-[4-(2-hydroxyethoxy)phenyl]ethyl}-1,3-oxazolidin-2-one (450 mg) in DCM (20 ml) at 0° C. under nitrogen was treated with diisopropylethylamine (0.23 ml) followed by methanesulphonyl chloride (0.09 ml) and the mixture was stirred at 0° C. for 1 h. Saturated NaHCO3 solution was added and the mixture was vigorously stirred for 5 min. The layers were separated and the organic phase washed with saturated NaHCO3 solution, dried (Na2SO4) and the solvent evaporated in vacuo to give the title compound (528 mg). LCMS RT=3.15 min.

Workup

stirringthe mixture was vigorously stirred for 5 min
customThe layers were separated
washthe organic phase washed with saturated NaHCO3 solution
dry with materialdried (Na2SO4)
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-fc3b2baaa7f7474aa08966f21c84e8d4
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271197B2

Reaction notes

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