Oxygen → HCID 14787654, compound

HRID 1253299Notes

Reaction equation

HRID 1253299 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:10][C:9]2[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=2[NH:7][C:6]1=[O:24])=[O:4].C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(C)C=CC=CC=1.[O:42]=O>O1CCCC1>[OH:42][C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH:11]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:10][C:9]2[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=2[NH:7][C:6]1=[O:24]

Participants

6

Reactant 4

HCID 977OxygenHCID 1140TolueneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 14156196HCID 14156196, compound

Product 1

HCID 14787654HCID 14787654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dry oxygen gas was bubbled through a cooled (ice bath) solution of 1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (13 g, 40.2 mmol) in 130 ml of dry tetrahydrofuran for 30 minutes. Potassium hexamethyldisilazide in toluene (180 ml, 0.67M, 120.5 mmol) was then added over a 7 minute period under a continuous stream of oxygen. After stirring for 2.5 hours, the oxygen flow was terminated and the reaction was quenched by the addition of 200 ml of 5% potassium bisulfate. Solid sodium sulfite (15 g) was then added followed by the addition of 100 ml of methanol and the mixture was stirred for an additional 30 minutes. The mixture was then extracted twice with ethyl acetate and the combined organic layers were washed three times with 1M hydrochloric acid, once with saturated bicarbonate solution followed by brine and then dried over sodium sulfate. Concentration afforded 15 g of crude product which was triturated with ether-hexane to yield 9.3 g of high purity product.

Workup

  1. customDry oxygen gas was bubbled through
  2. customthe oxygen flow was terminated
  3. customthe reaction was quenched by the addition of 200 ml of 5% potassium bisulfate
  4. additionSolid sodium sulfite (15 g) was then added
  5. additionfollowed by the addition of 100 ml of methanol
  6. stirringthe mixture was stirred for an additional 30 minutes
  7. extractionThe mixture was then extracted twice with ethyl acetate
  8. washthe combined organic layers were washed three times with 1M hydrochloric acid
  9. dry with materialdried over sodium sulfate
  10. concentrationConcentration
  11. customafforded 15 g of crude product which
  12. customwas triturated with ether-hexane

Sources & evidence

ORD record
ord-e67fec78078d436e942a046278db5c23
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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