Methanesulfonyl chloride → HCID 86619833, compound

HRID 658340Notes

Reaction equation

HRID 658340 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]1[CH:12]=[C:13]([C@@H:24]([OH:27])[CH2:25][OH:26])[C:14]2[S:18][C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[N:16][C:15]=2[CH:23]=1)([CH3:9])([CH3:8])[CH3:7]>N1C=CC=CC=1>[C:6]([O:10][C:11]1[CH:12]=[C:13]([C@@H:24]([OH:27])[CH2:25][O:26][S:2]([CH3:1])(=[O:4])=[O:3])[C:14]2[S:18][C:17]([O:19][CH:20]([CH3:21])[CH3:22])=[N:16][C:15]=2[CH:23]=1)([CH3:7])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66745065(1R)-1-[5-(1,1-Dimethylethoxy)-2-(1-methylethoxy)-7-benzothiazolyl]-1,2-ethanediol

Product 1

HCID 86619833HCID 86619833, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Methane sulfonylchloride (35 mg) is added to a solution of (R)-1-(5-tert-Butoxy-2-isopropoxy-benzothiazol-7-yl)-ethane-1,2-diol (100 mg) in pyridine (2 ml) at 0° C. The reaction mixture is then stirred at 0° C. for 3.5 hours. The solvent is removed in vacuo, The resulting residue is partitioned between HCl(aq) (2M) and ether. The organics is washed with water (1×), brine (1×), dried over MgSO4, filtered and the solvent removed in vacuo to give the title compound. 1H nmr (CDCl3, 400 MHz); 7.20 (d, 1H), 6.80 (d, 1H), 5.30 (sept, 1H), 5.10 (t, 1H), 4.30 (d, 2H), 3.00 (s, 3H), 1.40 (d, 6H), 1.30 (s, 9H).

Workup

  1. customThe solvent is removed in vacuo
  2. customThe resulting residue is partitioned between HCl(aq) (2M) and ether
  3. washThe organics is washed with water (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-25bfdf521a264a1696b57b19083b11dc
Source dataset
uspto-grants-2011_12
Patent number
US08076489B2

Reaction notes

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