Water → HCID 86760897, compound

HRID 1988252Notes

Reaction equation

HRID 1988252 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[NH:10][CH:11]([CH2:31][OH:32])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].O>N1C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:33])[NH:10][CH:11]([CH2:31][O:32][S:35]([CH3:34])(=[O:37])=[O:36])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:15]([C:27]([CH3:30])([CH3:28])[CH3:29])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 68866749HCID 68866749, compound

Product 1

HCID 86760897HCID 86760897, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(4-benzyloxy-3-t-butylphenyl)-1-hydroxymethylethylcarbamic acid benzyl ester (1.87 g, 4.18 mmol) in pyridine (42 ml), methanesulfonyl chloride (0.36 ml, 4.60 mmol) was added under cooling with ice. After stirring for 1 hour, the mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure, giving the titled compound (1.93 g, 88%).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-aa80e23bbc424f79ac6ea5df9ac99259
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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