Triethylamine → (3aR*,10aS*)-4-(Phthalimidoacetyl)-9-(4-propionamidobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 361577Notes

Reaction equation

HRID 361577 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(N(CC)CC)C.[C:45](Cl)(=[O:48])[CH2:46][CH3:47]>ClCCl.O>[C:21]1(=[O:30])[N:20]([CH2:19][C:18]([N:10]2[C@@H:11]3[CH2:17][CH2:16][CH2:15][C@@H:12]3[C:13](=[O:14])[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:45](=[O:48])[CH2:46][CH3:47])=[CH:37][CH:36]=3)[C:8]3[CH:35]=[CH:34][CH:33]=[CH:32][C:9]2=3)=[O:31])[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 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 67767989(3aR*,10aS*)-4-(Phthalimidoacetyl)-9-(4-propionamidobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (3aR*,10aS*)-9-(4-aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][l,4]diazepin-10(1H)-one (148 mg, 0.3 mmol) and triethylamine (50 μL, 0.36 mmol) in dichloromethane (3 mL) was added propionyl chloride (28 μL, 0.33 mmol) and the mixture was stirred at room temperature for 10 minutes. This reaction mixture was diluted with water and stirred. The aqueous layer was separated and the organic layer was dried over NaSO4 and concentrated under reduced pressure. The residue was crystallized from dichloromethane-ethanol-diethyl ether to provide 131 mg (yield 79%) of the title compound. m.p. 286.0°-286.5° C.

Workup

  1. stirringstirred
  2. customThe aqueous layer was separated
  3. dry with materialthe organic layer was dried over NaSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from dichloromethane-ethanol-diethyl ether

Sources & evidence

ORD record
ord-265c5f384d0d4cbdba604d00b76c034f
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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