Benzenesulfonyl chloride → HCID 22025358, compound

HRID 1792847Notes

Reaction equation

HRID 1792847 reaction equation
CCN(C(C)C)C(C)C.[Cl-].[NH2:11][CH:12]([CH2:26][C:27]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]2[C:28]=1[CH:29]=[CH:30][N:31]2[S:38]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(=[O:40])=[O:39])[C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:14].[C:47]1([S:53](Cl)(=[O:55])=[O:54])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(Cl)Cl.CCOCC>[C:47]1([S:53]([NH:11][CH:12]([CH2:26][C:27]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]3[C:28]=2[CH:29]=[CH:30][N:31]3[S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)(=[O:40])=[O:39])[C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:14])(=[O:55])=[O:54])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 131725860HCID 131725860, compound

Product 1

HCID 22025358HCID 22025358, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Hunig's base (2.1 g, 16 mmol) is added to a suspension of 2-amino-3-(1-benzenesulfonyl-7-methoxy-1H-indol-4-yl)-N-(4-phenyl-butyl)-propionamide, hydrogen chloride salt (3.0 g, 5.6 mmol) in CH2Cl2. The resulting solution is cooled to 0° C. and benzenesulfonyl chloride (1.2 g, 6.9 mmol) is added. After being warmed to rt and stirred 2 h, the reaction mixture is diluted with Et2O and washed sequentially with 0.5 M HCl and saturated NaHCO3 solutions. The aqueous phases are extracted once with Et2O. The desired compound crystallizes at this point. The volatiles are removed in vacuo and the remaining residue is azeotroped sequentially with dioxane and toluene to provide 2-benzenesulfonylamino-3-(1-benzenesulfonyl-7-methoxy-1H-indol-4-yl)-N-(4-phenyl-butyl)-propionamide as a solid which is used as is without further purification.

Workup

  1. temperatureAfter being warmed to rt
  2. washwashed sequentially with 0.5 M HCl and saturated NaHCO3 solutions
  3. extractionThe aqueous phases are extracted once with Et2O
  4. customThe desired compound crystallizes at this point
  5. customThe volatiles are removed in vacuo
  6. customthe remaining residue is azeotroped sequentially with dioxane and toluene

Sources & evidence

ORD record
ord-abb7f6e090d74c539d90ada5554ca473
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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