Water → HCID 86760898, compound

HRID 1988254Notes

Reaction equation

HRID 1988254 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.[C:34]1([CH3:44])[C:35]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:37]=[CH:38][CH:39]=1.O>N1C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:33])[NH:10][CH:11]([CH2:31][O:32][S:40]([C:35]1[C:34]([CH3:44])=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:42])=[O:41])[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 8623o-Toluenesulfonyl chlorideHCID 68866749HCID 68866749, compound

Product 1

HCID 86760898HCID 86760898, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(4-benzyloxy-3-t-butylphenyl)-1-hydroxymethylethylcarbamic acid benzyl ester (2.07 g, 4.63 mmol) in pyridine (46 ml), toluenesulfonyl chloride (6.79 g, 35.6 mmol) was added under cooling with ice. After stirring for 6.5 hours, 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; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1), giving the titled compound (2.46 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-d0ca56724306476e90a087e1e81e9e9c
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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