Water → 2-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxy-1-methanesulfonyloxybutane

HRID 1975458Notes

Reaction equation

HRID 1975458 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH3:13])[CH2:10][OH:11])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>ClCCl>[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:12]([O:14][Si:15]([C:18]([CH3:20])([CH3:19])[CH3:21])([CH3:16])[CH3:17])[CH3:13])[CH2:10][O:11][S:30]([CH3:29])(=[O:32])=[O:31])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 190993042-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxybutan-1-ol

Product 1

HCID 190992922-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxy-1-methanesulfonyloxybutane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.00 g of 2-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxybutan-1-ol and 4.60 ml of triethylamine in 35 ml of dichloromethane was added dropwise 2.05 ml of methanesulfonyl chloride at -10° C. After stirring for 3 hours, water was added to the reaction mixture and then the solution was extracted with chloroform. The organic layer was washed in turn with 1N hydrochloric acid and brine, and dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by a column chromatography on silica gel (hexane:ethyl acetate=3:1) gave 8.8 g of 2-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxy-1-methanesulfonyloxybutane.

Workup

  1. extractionthe solution was extracted with chloroform
  2. washThe organic layer was washed in turn with 1N hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-269551bf851f43f3837d408f9e7ddef1
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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