Water → HCID 21962370, compound

HRID 1821485Notes

Reaction equation

HRID 1821485 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-742753a36922415f94999268d00e4d5d
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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