Benzenesulfonyl chloride → (3aR*,10aS*)-9-[(4-Benzenesulfonamido)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 361578Notes

Reaction equation

HRID 361578 reaction equation
Br.N[C:3]1[CH:38]=[CH:37][C:6]([CH2:7][N:8]2[C:14](=[O:15])[C@H:13]3[CH2:16][CH2:17][CH2:18][C@H:12]3[N:11]([C:19](=[O:32])[CH2:20][N:21]3[C:25](=[O:26])[C:24]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]4[C:22]3=[O:31])[C:10]3[CH:33]=[CH:34][CH:35]=[CH:36][C:9]2=3)=[CH:5][CH:4]=1.[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C([N:51](CC)CC)C.C([O-])(O)=O.[Na+]>ClCCCl>[CH:42]1[CH:43]=[CH:44][C:39]([S:45]([NH:51][CH:7]([N:8]2[C:14](=[O:15])[C@H:13]3[CH2:16][CH2:17][CH2:18][C@H:12]3[N:11]([C:19](=[O:32])[CH2:20][N:21]3[C:25](=[O:26])[C:24]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]4[C:22]3=[O:31])[C:10]3[CH:33]=[CH:34][CH:35]=[CH:36][C:9]2=3)[C:6]2[CH:37]=[CH:38][CH:3]=[CH:4][CH:5]=2)(=[O:47])=[O:46])=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67767990(3aR*,10aS*)-9-(4-Aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-one hydrobromide

Product 1

HCID 67767520(3aR*,10aS*)-9-[(4-Benzenesulfonamido)benzyl]-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 50%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (3aR*,10aS*)-9-(4-aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one hydrobromide (200 mg, 0.35 mmol) in 1,2-dichloroethane (30 mL) was added benzenesulfonyl chloride (61 mg, 0.35 mmol) as well as triethylamine (0.055 mL, 0.40 mmol) and the mixture was stirred at room temperature for 1.5 hours. After addition of saturated aqueous NaHCO3 solution, the aqueous layer was separated and the organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated under reduced pressure to remove the solvent. The residue was crystallized from diethyl ether to provide 110 mg (yield 50%) of the title compound. m.p. 212°-214° C.

Workup

  1. customthe aqueous layer was separated
  2. washthe organic layer was washed with saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto remove the solvent
  6. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-bb0b813c215f47d392f27661bc765bfc
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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