Methanesulfonyl chloride → HCID 86674089, compound

HRID 337230Notes

Reaction equation

HRID 337230 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:17][C:18](=[O:28])[NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH2:10]([O:17][C:18]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][O:27][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:24][CH:25]=1)=[O:28])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 64793016HCID 64793016, compound

Product 1

HCID 86674089HCID 86674089, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.19 ml, 1.17 mmol) was added to a cool (0° C.) solution of (4-Hydroxymethyl-phenyl)-carbamic acid benzyl ester (0.25 g, 0.97 mmol) in DCM (8 ml) and the reaction stirred at this temperature for 5 minutes. After this time, methane sulfonyl chloride (0.09 ml, 1.07 mmol) was added dropwise and the mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was then diluted with DCM (20 ml) and washed sequentially with saturated sodium bicarbonate solution (10 ml), saturated ammonium chloride (10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compound (0.29 g, 89% yield) as a yellow oil which was taken forward without further purification.

Workup

  1. stirringstirred for 1 hour
  2. washwashed sequentially with saturated sodium bicarbonate solution (10 ml), saturated ammonium chloride (10 ml) and brine (10 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3a55568aabed4e3390eb1e20ccdc0448
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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