2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo- → (3aR*,10aS*)-9-Benzyl-4-(phthalimidoacetyl)-1,2,3,3a,4,9,10,10a-octahydrobenzo[b]cyclopenta [e][1,4]diazepin

HRID 356156

反応式

HRID 356156 の反応式
[CH2:1]([N:8]1[C:14](=O)[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[NH:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(=[O:37])[N:27]([CH2:28][C:29](Cl)=[O:30])[C:26](=[O:32])[C:25]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:24]12.C(=O)([O-])O.[Na+]>ClCCCl>[CH2:1]([N:8]1[CH2:14][C@@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:29](=[O:30])[CH2:28][N:27]2[C:26](=[O:32])[C:25]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:24]3[C:23]2=[O:37])[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 516892Sodium BicarbonateHCID 70109795(3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta [e][1,4]diazepin-10(1H)-one

生成物 1

HCID 70110880(3aR*,10aS*)-9-Benzyl-4-(phthalimidoacetyl)-1,2,3,3a,4,9,10,10a-octahydrobenzo[b]cyclopenta [e][1,4]diazepin収率 37%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A crude product of (3aR*,10aS*)-9-benzyl-4-1,2,3,3a,4,9,10,10a-octahydrobenzo[b]cyclopenta-[e][1,4]diazepin synthesized from (3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta [e][1,4]diazepin-10(1H)-one (2.92 g, 10 mmol) in substantially the same manner as in Working Example 42 was dissolved in 1,2-dichloroethane, to which was added phthalimidoacetyl chloride (2.24 g, 10 mmol). The mixture was stirred for 15 minutes at room temperature, which was refluxed for 15 minutes. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate (15 mL). The aqueous layer was separated, and the organic layer was washed with water and, then, dried over magnesium sulfate, which was subject to filtration, followed by concentration under reduced pressure. To the concentrate was added ethanol-diethylether, and the solid matter was collected by filtration and recrystallized from chloroform-ethanol to give 1.72 g (yield 37%) of the titled compound, m.p. 232°-234° C.

後処理

  1. temperaturewhich was refluxed for 15 minutes
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate, which
  5. filtrationwas subject to filtration
  6. concentrationfollowed by concentration under reduced pressure
  7. additionTo the concentrate was added ethanol-diethylether
  8. filtrationthe solid matter was collected by filtration
  9. customrecrystallized from chloroform-ethanol

出典と根拠

ORDレコード
ord-975ed200d9f343508b4bd508b157cbad
出典データセット
uspto-grants-1998_11
特許番号
US05834463

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