Water → HCID 70111903, compound

HRID 356167Notes

Reaction equation

HRID 356167 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:33])[CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:32])[C:10]2[CH:34]=[CH:35][CH:36]=[CH:37][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:33])[CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[C:27]([O:31][CH3:38])[CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:32])[C:10]2[CH:34]=[CH:35][CH:36]=[CH:37][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 70112105(3aR*,10aS*)-9-benzyl-4-((3-hydroxyphthalimido)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 70111903HCID 70111903, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (3aR*,10aS*)-9-benzyl-4-((3-hydroxyphthalimido)acetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (343 mg, 0.69 mmol) in N,N-dimethylformamide (3 mL) were added potassium carbonate (115 mg, 0.83 mmol) and methyl iodide (0.10 mL, 1.6 mmol). The mixture was stirred for 4.5 hours at room temperature, to which was added water. The resulting solid was separated by filtration, and the filtrate was subjected to extraction with chloroform. In this organic layer was dissolved the solid previously separated by filtration. The solution was dried over magnesium sulfate, which was subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was recrystallized from chloroform-diethylether to give 340 mg (yield 96%) of the titled compound, m.p. 247°-248° C.

Workup

  1. customThe resulting solid was separated by filtration
  2. extractionthe filtrate was subjected to extraction with chloroform
  3. dissolutionIn this organic layer was dissolved the solid
  4. custompreviously separated by filtration
  5. dry with materialThe solution was dried over magnesium sulfate, which
  6. filtrationwas subjected to filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe concentrate was recrystallized from chloroform-diethylether

Sources & evidence

ORD record
ord-7ffb326f14214447a14bda5bd791fadc
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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