Triethylamine → HCID 86614643, compound

HRID 1445841Notes

Reaction equation

HRID 1445841 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[O:23][C:24]([CH3:31])=[C:25]([CH2:27][CH2:28][CH2:29][OH:30])[N:26]=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].C(N(CC)CC)C>ClCCl>[CH3:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[O:23][C:24]([CH3:31])=[C:25]([CH2:27][CH2:28][CH2:29][O:30][S:2]([CH3:1])(=[O:4])=[O:3])[N:26]=3)=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68704871HCID 68704871, compound

Product 1

HCID 86614643HCID 86614643, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (0.086 g, 0.60 mmol) to a cool (0° C.) solution of 3-[2-(4′-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-propan-1-ol (0.170 g, 0.458 mmol) and triethylamine (0.070 g, 0.69 mmol) in dichloromethane (3 mL). Warm the reaction mixture to room temperature and stir for 1 hour. Add dichloromethane and wash the crude organic material with saturated sodium chloride solution. Dry the organic extracts over Na2SO4, filter, and concentrate to give crude methanesulfonic acid 3-[2-(4′-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-propyl ester (0.206 g, 100%): MS (m/e): 450(M+1).

Workup

  1. washAdd dichloromethane and wash the crude organic material with saturated sodium chloride solution
  2. dry with materialDry the organic extracts over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-9e858eea9e7d4397a22a6cd13379f466
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…