Water → HCID 11307499, compound

HRID 750946Notes

Reaction equation

HRID 750946 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH:8]=[CH:9][N:10]=1.Cl[CH2:23][C:24]1[N:25]=[C:26]([CH:29]=[CH:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([C:39]([F:42])([F:41])[F:40])=[O:38])=[CH:33][CH:32]=2)[O:27][CH:28]=1.O>CN(C=O)C>[F:42][C:39]([F:40])([F:41])[S:37]([C:34]1[CH:35]=[CH:36][C:31](/[CH:30]=[CH:29]/[C:26]2[O:27][CH:28]=[C:24]([CH2:23][O:21][C:18]3[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:7]4[CH:8]=[CH:9][N:10]=[C:6]4[CH2:5][CH2:4][OH:3])=[CH:20][CH:19]=3)[N:25]=2)=[CH:32][CH:33]=1)=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 222593234-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenolHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

Product 1

HCID 11307499HCID 11307499, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13.0 mg (0.50 mmol) 95% sodium hydride were given to a solution of 130 mg (0.50 mmol) 4-{4-[2-(2-Hydroxyethyl)-imidazol-1-yl]-butyl}-phenol in 4.0 ml DMF and stirred for 15 min. 168 mg (0.50 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole were added and stirring continued at r.t. overnight. After addition of 10 ml water the resulting precipitate was washed twice with water, 10 ml methanol/water 1:1 and with diethyl ether. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/methanol 9:1) to yield 99 mg colorless powder that was further purified by HPLC-MS.

Workup

  1. stirringstirring
  2. waitcontinued at r.t. overnight
  3. washwas washed twice with water, 10 ml methanol/water 1:1 and with diethyl ether
  4. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-1cd8ec5095224561907bbd0329afe7f5
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

Loading…