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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 356189
ノート
印刷プレビュー

反応式

HRID 356189 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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)-one収率 61%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cf91e8598254a44aaf09e6b1d769b00
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05834463

反応ノート

読み込み中…

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