Methanesulfonyl chloride → (S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methylsulfonyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 451825Notes

Reaction equation

HRID 451825 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([CH2:26][CH2:27][OH:28])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@H:10]([CH2:26][CH2:27][O:28][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68712820(S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-hydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 86639451(S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methylsulfonyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-hydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylate and TEA in CH2Cl2 at 0° C. was added dropwise a solution of MsCl. The mixture was stirred for 2 h. The mixture was washed with water and dried over Na2SO4. The organic phase was distilled off to give the crude product (S)-tert-butyl 4-((S)-2-((tert-butyldimethylsilyloxy)methyl)-4-(methylsulfonyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate (6.2 g). 1H NMR (CDCl3, 400 MHz) δ 0.06 (s, 6H, 0.89 (s, 9H), 1.46 (s, 12H), 1.50 (s, 3H), 1.53 (m, 3H), 2.94 (s, 3H), 3.49 (m, 2H), 3.50 (m, 2H), 3.7 (m, 2H), 3.9 (m, 1H).

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. distillationThe organic phase was distilled off

Sources & evidence

ORD record
ord-eaf79391166241bfa0cbcabbb338536b
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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