Water → HCID 21962370, compound

HRID 2212751Notes

Reaction equation

HRID 2212751 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]([C:47]3[CH:48]=[C:49]([CH:54]=[CH:55][CH:56]=3)[C:50]([O:52][CH3:53])=[O:51])=[CH:43][CH:42]=2)(=[O:40])=[O:39])=[C:27]1[CH2:57][CH2:58][OH:59])([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:46]=[CH:45][C:44]([C:47]3[CH:48]=[C:49]([CH:54]=[CH:55][CH:56]=3)[C:50]([O:52][CH3:53])=[O:51])=[CH:43][CH:42]=2)(=[O:40])=[O:39])=[C:27]1[CH2:57][CH2:58][O:59][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:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21962390HCID 21962390, compound

Product 1

HCID 21962370HCID 21962370, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CH3SO2Cl (2 eq) and Et3N (2.5 eq) were added to a solution of methyl 3-[4-({2-[1-benzhydryl-5-chloro-2-(2-hydroxyethyl)-1H-indol-3-yl]ethyl}sulfonyl)phenyl]benzoate (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 methyl 3-(4-{[2-(1-benzhydryl-5-chloro-2-{2-[(methylsulfonyl)oxy]ethyl}-1H-indol-3-yl)ethyl]sulfonyl}phenyl)benzoate (light-yellow solid) in 99% yield.

Workup

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

Sources & evidence

ORD record
ord-1e56527d2c25435a8afdb0f01739a222
Source dataset
uspto-grants-2006_09
Patent number
US07101875B2

Reaction notes

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