Benzenesulfonyl chloride → HCID 11856614, compound

HRID 502554Notes

Reaction equation

HRID 502554 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:10]([NH:12][CH2:13][CH2:14][NH:15][C:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[S:18][N:17]=1)=[O:11].C(N(CC)CC)C.[C:38]1([S:44](Cl)(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>ClCCl>[S:18]1[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:16]([NH:15][CH2:14][CH2:13][NH:12][C:10](=[O:11])[C@H:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:8][S:44]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:46])=[O:45])=[N:17]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 68461491HCID 68461491, compound

Product 1

HCID 11856614HCID 11856614, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(S)-2-amino-N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)-2-phenyl-acetamide trifluoroacetate salt (100 mg, 0.31 mmol) was dissolved in anhydrous dichloromethane (5 mL) with triethylamine (52 μL, 0.37 mmol). The solution was cooled on an ice-water bath and then a solution of benzenesulfonyl chloride (47 μL, 0.37 mmol) in dichloromethane (0.5 mL) was added dropwise. The reaction mixture was allowed to stir overnight while warming to room temperature. The solution was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, then dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure. Purification by column chromatography, on silica gel, eluting with a mixture of 30% ethyl acetate in hexanes, and selected fractions were combined and concentrated under reduced pressure to yield (S)-N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)-2-phenyl-2-(phenylsulfonamido)acetamide (26 mg) as a white solid. 1H NMR (300 MHz, CDCl3): 7.78 (d, 1H), 7.70 (t, 3H), 7.48 (m, 2H), 7.38 (q, 3H), 7.10 (m, 5H), 6.00 (d, 1H), 5.90 (broad s, 1H), 4.78 (d, 1H), 3.63 (broad s, 2H), 3.52 ppm (m, 2H). MW=467 confirmed by LC-MS, tr=3.94 min (Method B) MH+=468.

Workup

  1. temperatureThe solution was cooled on an ice-water bath
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customPurification by column chromatography
  7. washon silica gel, eluting with a mixture of 30% ethyl acetate in hexanes
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe53f5880cf14f5dba21eaaaf4590fa4
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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