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

반응식

HRID 356156 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-975ed200d9f343508b4bd508b157cbad
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834463

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