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 361578노트

반응식

HRID 361578 반응식
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

참가 물질

6

반응물 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

생성물 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)-one수율 50%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bb0b813c215f47d392f27661bc765bfc
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866567

반응 노트

불러오는 중…