Water → HCID 21962238, compound

HRID 2212749Notes

Reaction equation

HRID 2212749 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(CC)CC.[CH:13]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=2)[C:28]([CH2:36][CH2:37][S:38]([C:41]2[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:43][CH:42]=2)(=[O:40])=[O:39])=[C:27]1[CH2:54][CH2:55][OH:56])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C(Cl)Cl>[CH:13]([N:26]1[C:34]2[C:29](=[CH:30][C:31]([Cl:35])=[CH:32][CH:33]=2)[C:28]([CH2:36][CH2:37][S:38]([C:41]2[CH:42]=[CH:43][C:44]([CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:45][CH:46]=2)(=[O:39])=[O:40])=[C:27]1[CH2:54][CH2:55][O:56][S:2]([CH3:1])(=[O:4])=[O:3])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21962304HCID 21962304, compound

Product 1

HCID 21962238HCID 21962238, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CH3SO2Cl (2 eq) and Et3N (2.5 eq) were added to a solution of ethyl 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-hydroxyethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]propanoate (1 eq) in CH2Cl2 (0.02M) at 0° C. under N2. After 1 hour the reaction was warmed to room temperature. After an additional hour water was added and extracted with CH2Cl2 and washed with brine and dried over sodium sulfate. Removed solvent to obtain ethyl 3-(4-{[2-(1-benzhydryl-5-chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-1H-indol-3-yl)ethyl]sulfonyl}phenyl)propanoate (white solid) in 98% yield.

Workup

  1. extractionextracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-78d3083863624a3caf801d0eded5aa2d
Source dataset
uspto-grants-2006_09
Patent number
US07101875B2

Reaction notes

Loading…