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

HRID 356189Notes

Reaction equation

HRID 356189 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[C@@H:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[C:9](=[O:15])[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[CH:23]=[CH:24][CH:25]=[CH:26][C:6]1=2)=[O:4].[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[C:27]1([S:33]([NH:1][CH2:2][C:3]([N:5]2[C@@H:11]3[CH2:12][CH2:13][CH2:14][C@@H:10]3[C:9](=[O:15])[N:8]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:7]3[CH:23]=[CH:24][CH:25]=[CH:26][C:6]2=3)=[O:4])(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 70110459(3aR*,10aS*)-4-(Aminoacetyl)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 70113429(3aR*,10aS*)-4-((Benzenesulfonamido)acetyl)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-oneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3aR*,10aS*)-4-aminoacetyl-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta-[e][1,4]diazepin-10(1H)-one (0.2 g, 0.57 mmol) and benzenesulfonyl chloride (0.12 g, 0.69 mmol) in dichloromethane (10 mL) was added triethylamine (70 mg, 0.69 mmol). The mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate, which was subjected to extraction with dichloromethane. The extract was washed with water and dried, then, the solvent was distilled off. The residue was purified by silica-gel column chromatography (dichloromethane), which was crystallized from diethyl ether to give 170 mg (yield 61%) of the titled compound, m.p. 185°-187° C.

Workup

  1. extractionwas subjected to extraction with dichloromethane
  2. washThe extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica-gel column chromatography (dichloromethane), which
  6. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-3cf91e8598254a44aaf09e6b1d769b00
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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