Ammonium cerium (IV) nitrate → HCID 70111246, compound

HRID 356161

Reaction equation

HRID 356161 reaction equation
C[O:2][C:3]1[C:38]([CH3:39])=[C:37]([CH3:40])[C:36]([O:41]C)=[C:35]([CH3:43])[C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[C@H:11]2[CH2:14][CH2:15][CH2:16][C@H:10]2[N:9]([C:17](=[O:30])[CH2:18][N:19]2[C:23](=[O:24])[C:22]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]3[C:20]2=[O:29])[C:8]2[CH:31]=[CH:32][CH:33]=[CH:34][C:7]1=2.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(#N)C.O>[C:20]1(=[O:29])[N:19]([CH2:18][C:17]([N:9]2[C@@H:10]3[CH2:16][CH2:15][CH2:14][C@@H:11]3[C:12](=[O:13])[N:6]([CH2:5][C:4]3[C:3](=[O:2])[C:38]([CH3:39])=[C:37]([CH3:40])[C:36](=[O:41])[C:35]=3[CH3:43])[C:7]3[CH:34]=[CH:33][CH:32]=[CH:31][C:8]2=3)=[O:30])[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]12

Participants

5

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 86753321HCID 86753321, compound

Product 1

HCID 70111246HCID 70111246, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolvent2×

Procedure

In a mixture of acetonitrile (3 mL) and water (2 mL) was suspended (3aR*,10aS*)-9-(2,5-dimethoxy-3,4,6-trimethylbenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (0.5 g, 0.86 mmol). To the suspension was added, while stirring, a solution of ammonium cerium (IV) nitrate (1.4 g, 2.55 mmol) in a mixture of acetonitrile (2 mL) and water (2 mL). The reaction mixture was stirred for one hour, which was diluted with water, followed by extraction with chloroform. The extract was washed with water and dried, then the solvent was distilled off. The residue was crystallized from ethyl acetate to give 300 mg (yield 63%) of the titled compound, m.p. 258°-260° C.

Workup

  1. additionTo the suspension was added
  2. stirringThe reaction mixture was stirred for one hour
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-847abb0f88834618ac59ca324403a869
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Linked notes

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