Acetyl chloride → (3aR*,10aS*)-9-(4-Acetamidobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-one

HRID 361576Notes

Reaction equation

HRID 361576 reaction equation
[NH2:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][N:7]2[C:13](=[O:14])[C@H:12]3[CH2:15][CH2:16][CH2:17][C@H:11]3[N:10]([C:18](=[O:31])[CH2:19][N:20]3[C:24](=[O:25])[C:23]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]4[C:21]3=[O:30])[C:9]3[CH:32]=[CH:33][CH:34]=[CH:35][C:8]2=3)=[CH:4][CH:3]=1.[C:38](Cl)(=[O:40])[CH3:39].C([O-])(O)=O.[Na+]>ClCCl>[C:38]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:13](=[O:14])[C@H:12]3[CH2:15][CH2:16][CH2:17][C@H:11]3[N:10]([C:18](=[O:31])[CH2:19][N:20]3[C:21](=[O:30])[C:22]4=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]4[C:24]3=[O:25])[C:9]3[CH:32]=[CH:33][CH:34]=[CH:35][C:8]2=3)=[CH:36][CH:37]=1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 54523300(3aR*,10aS*)-9-(4-aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][l,4]diazepin-10(1H)-one

Product 1

HCID 67767992(3aR*,10aS*)-9-(4-Acetamidobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e]-[1,4]diazepin-10(1H)-oneYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of (3aR*,10aS*)-9-(4-aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (198 mg, 0.4 mmol) in dichloromethane (1 mL) was added acetyl chloride (43 μL, 0.6 mmol) and the mixture was stirred at room temperature for 20 minutes. This reaction mixture was diluted with dichloromethane (3 mL) and, after saturated aqueous NaHCO3 solution (2 mL) was added, the mixture was further stirred. The aqueous layer was then separated and the organic layer was washed with water, dried over MgSO4, and concentrated under reduced pressure. The residue was crystallized from dichloromethane-ethanol and recrystallized from chloroform-ethanol to provide 72 mg (yield 34%) of the title compound. m.p. 303°-306° C.

Workup

  1. customThe aqueous layer was then separated
  2. washthe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from dichloromethane-ethanol
  6. customrecrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-f6883a3bd5b742119ebcfdde388eefee
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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