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

Reaction equation

HRID 356156 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-975ed200d9f343508b4bd508b157cbad
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Linked notes

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