Water → HCID 70111957, compound

HRID 356203Notes

Reaction equation

HRID 356203 reaction equation
COC1C=CC(C[N:8]2[C:14](=[O:15])[C@H:13]3[CH2:16][CH2:17][CH2:18][C@H:12]3[N:11]([C:19](=[O:32])[CH2:20][N:21]3[C:25](=[O:26])[C:24]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]4[C:22]3=[O:31])[C:10]3[CH:33]=[CH:34][CH:35]=[CH:36][C:9]2=3)=CC=1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.O>C(Cl)(Cl)Cl.C(#N)C>[C:22]1(=[O:31])[N:21]([CH2:20][C:19]([N:11]2[C@@H:12]3[CH2:18][CH2:17][CH2:16][C@@H:13]3[C:14](=[O:15])[NH:8][C:9]3[CH:36]=[CH:35][CH:34]=[CH:33][C:10]2=3)=[O:32])[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]12

Participants

6

Reactant 3

HCID 962Water2×HCID 9869224Ammonium cerium (IV) nitrateHCID 70111310HCID 70111310, compound

Product 1

HCID 70111957HCID 70111957, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (3aR*,10aS*)-9-(4-methoxybenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (9.89 g, 19 mmol) in chloroform (150 mL) was added a solution of ammonium cerium (IV) nitrate (31.3 g, 57 mmol) and water (5 mL) in acetonitrile (150 mL), and the mixture was stirred for 10 minutes at room temperature. The reaction mixture was poured into water (300 mL), which was subjected to extraction twice with chloroform. Organic layers were combined, washed with water and a saturated aqueous solution of sodium hydrogencarbonate, dried over magnesium sulfate and subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was purified by silica-gel column chromatography (chloroform-ethyl acetate 2:1) to a crystalline product, which was washed with chloroform-diisopropyl ether to give 3.7 g (yield 50%) of the titled compound.

Workup

  1. extractionwas subjected to extraction twice with chloroform
  2. washwashed with water
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, dried over magnesium sulfate
  4. filtrationsubjected to filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe concentrate was purified by silica-gel column chromatography (chloroform-ethyl acetate 2:1) to a crystalline product, which
  7. washwas washed with chloroform-diisopropyl ether

Sources & evidence

ORD record
ord-1cbd4c31df654fd49b061c3dc08343c6
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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