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 361578ノート

反応式

HRID 361578 の反応式
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

参加物

6

反応物 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

生成物 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)-one収率 50%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb0b813c215f47d392f27661bc765bfc
出典データセット
uspto-grants-1999_02
特許番号
US05866567

反応ノート

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