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

HRID 356215Notes

Reaction equation

HRID 356215 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[C:20](=[O:21])[C@H:19]3[CH2:22][CH2:23][CH2:24][C@H:18]3[NH:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]1(=[O:45])[N:35]([CH2:36][C:37](Cl)=[O:38])[C:34](=[O:40])[C:33]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:32]12.C(=O)([O-])O.[Na+]>ClCCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:20](=[O:21])[C@H:19]3[CH2:22][CH2:23][CH2:24][C@H:18]3[N:17]([C:37](=[O:38])[CH2:36][N:35]3[C:34](=[O:40])[C:33]4=[CH:41][CH:42]=[CH:43][CH:44]=[C:32]4[C:31]3=[O:45])[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]2=3)=[CH:29][CH:30]=1)[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 70112136HCID 70112136, compound

Product 1

HCID 70111813(3aR*,10aS*)-9-(4-Benzyloxybenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 42%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (3aR*,10aS*)-9-(4-benzyloxybenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b ]cyclopenta[e][1,4]diazepin-10(1H)-one (3.1 g, 7.8 mmol) in 1,2-dichloroethane was added phthalimidoacetyl chloride (1.9 g, 8.5 mmol). The mixture was refluxed for 17 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was separated. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was parified by silica-gel column chromatography (hexane-ethyl acetate 1:3), which was crystallized from diethyl ether to give the desired product (1.9 g, 42%), m.p.179°-181° C.

Workup

  1. temperatureThe mixture was refluxed for 17 hours
  2. customThe aqueous layer was separated
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationsubjected to filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-6d6cfae5ad004ad1a035c63bf411a79f
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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