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Water → (3aR*,10aS*)-9-Benzyl-4-((4-chlorophthalimido)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one

HRID 356163
Notes
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Reaction equation

HRID 356163 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[C@@H:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[C:9](=[O:15])[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[CH:23]=[CH:24][CH:25]=[CH:26][C:6]1=2)=[O:4].[Cl:27][C:28]1[CH:29]=[C:30]2[C:35](=O)[O:34][C:32](=[O:33])[C:31]2=[CH:37][CH:38]=1.O.CCCCCC>C1(C)C=CC=CC=1>[CH2:16]([N:8]1[C:9](=[O:15])[C@H:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[N:5]([C:3](=[O:4])[CH2:2][N:1]2[C:35](=[O:34])[C:30]3=[CH:29][C:28]([Cl:27])=[CH:38][CH:37]=[C:31]3[C:32]2=[O:33])[C:6]2[CH:26]=[CH:25][CH:24]=[CH:23][C:7]1=2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 670444-Chlorophthalic anhydrideHCID 70110459(3aR*,10aS*)-4-(Aminoacetyl)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 70113637(3aR*,10aS*)-9-Benzyl-4-((4-chlorophthalimido)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one
Yield 75.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of (3aR*,10aS*)-4-(aminoacetyl)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta-[e][1,4]diazepin-10(1H)-one (0.58 g, 1.7 mmol) and 4-chlorophthalic anhydride (0.31 g, 1.7 mmol) in toluene (10 mL) was refluxed for 3.5 hours using a Dean-Stark water separator. The reaction mixture was left standing for cooling at room temperatures, to which was added hexane. The resulting solid was collected by filtration, which was recrystallized from chloroform-hexane to give 0.66 g (yield 75%) of the titled compound, m.p. 237°-238° C.

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. waitThe reaction mixture was left
  3. temperaturefor cooling at room temperatures, to which
  4. filtrationThe resulting solid was collected by filtration, which
  5. customwas recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-11ec5e38c09148f997f7f2d6829245da
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834463

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes