Water → HCID 21962238, compound

HRID 988892Notes

Reaction equation

HRID 988892 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-1775fd37ba08407aa72befdc8ac9e434
Source dataset
uspto-grants-2003_10
Patent number
US06635771B2

Reaction notes

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