Water → HCID 70113137, compound

HRID 356170Notes

Reaction equation

HRID 356170 reaction equation
[C:1]1(=[O:29])[N:5]([CH2:6][C:7]([N:9]2[C@@H:15]3[CH2:16][CH2:17][CH2:18][C@@H:14]3[C:13](=[O:19])[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[O:8])[C:4](=[O:24])[C:3]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]12.[H-].[Na+].Cl[CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1.O>CN(C)C=O>[C:34]1([CH2:33][N:12]2[C:13](=[O:19])[C@H:14]3[CH2:18][CH2:17][CH2:16][C@H:15]3[N:9]([C:7](=[O:8])[CH2:6][N:5]3[C:4](=[O:24])[C:3]4=[CH:25][CH:26]=[CH:27][CH:28]=[C:2]4[C:1]3=[O:29])[C:10]3[CH:23]=[CH:22][CH:21]=[CH:20][C:11]2=3)[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 70111957HCID 70111957, compound

Product 1

HCID 70113137HCID 70113137, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
28 °C

Procedure

To a suspension of (3aR*,10aS*)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (391 mg, 1.0 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (60% liquid paraffin dispersion, 44 mg, 1.1 mmol). The mixture was stirred for 10 minutes at 28° C., to which was added 1-(chloromethyl) naphthalene(213 mg, 1.2 mmol), followed by stirring for 20 minutes at the same temperature. To the reaction mixture was added water (5 mL), and the mixture was subjected to extraction twice with chloroform. The organic layers were combined and washed with water, dried over magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was crystallized from ethanol to give 177 mg (yield 33%) of the titled compound, m.p. 266°-270° C.

Workup

  1. stirringby stirring for 20 minutes at the same temperature
  2. extractionthe mixture was subjected to extraction twice with chloroform
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfollowed by filtration and concentration under reduced pressure
  6. customThe concentrate was crystallized from ethanol

Sources & evidence

ORD record
ord-9bd97e5ab47642948b3c790c7a6fcffa
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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