Methanesulfonyl chloride → HCID 86759216, compound

HRID 987931Notes

Reaction equation

HRID 987931 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]([OH:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]([O:28][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:10][C:9]1([CH3:29])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69853737HCID 69853737, compound

Product 1

HCID 86759216HCID 86759216, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-benzyl-5-(3-ethoxycarbonyl-2-hydroxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (50.68 g) in pyridine (380 ml) was stirred at 15° C. under an atmosphere of nitrogen during the dropwise addition of methanesulfonyl chloride (18.4 ml). The reaction mixture was then allowed to warm to ambient temperature and stirred for a further 2 hours and evaporated. The residue was dissolved in diethyl ether, washed sequentially with 2M aqueous hydrochloric acid (500 ml and 250 ml), water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate) and evaporated to afford 4-benzyl-5-(3-ethoxycarbonyl-2-methanesulfonyloxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (64 g) as a pale yellow gum Mass spectrum 500 [M+H]+.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in diethyl ether
  3. washwashed sequentially with 2M aqueous hydrochloric acid (500 ml and 250 ml), water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-f9b50029431e4079aec6597136c7f6f9
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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