Sodium Phosphate, Dibasic → Methyl cis-3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate

HRID 1974182

반응식

HRID 1974182 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:12](=[O:13])[N:11](CC2C=CC(OC)=CC=2OC)[CH:10]1[C:25]([O:27][CH3:28])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[Na+].[Na+]>C(#N)C.O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:12](=[O:13])[NH:11][C@H:10]1[C:25]([O:27][CH3:28])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 24203Sodium Phosphate, DibasicHCID 24412Potassium PersulfateHCID 23470103Methyl 3-t-butoxycarbonylamino-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate

생성물 1

HCID 70428372Methyl cis-3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A solution of 10.5 g (26.7 mmole) of methyl 3-t-butoxycarbonylamino-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate in 500 ml of acetonitrile was degassed with argon and warmed to 80°. A degassed solution of 15 g (55.5 mmole) of potassium persulfate and 7.5 g (28 mmole) of sodium monohydrogen phosphate in 150 ml of water was added in five portions over 1 hour. The reaction was stirred at 80°-85° under argon for 2-3 hours until all starting material had disappeared (tlc). The reaction mixture was cooled, concentrated in vacuo and shaken with ethyl-acetate water. The organic phase was washed with dilute hydrochloric acid, aqueous sodium bicarbonate solution and brine, dried (MgSO4) and evaporated to dryness. The residue was chromatographed on silica gel with 1:1 benzene:ethyl acetate to afford pure product which crystallized from ethyl acetate-hexane to give methyl cis-3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate, mp 140°-144°.

후처리

  1. temperaturewarmed to 80°
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. stirringshaken with ethyl-acetate water
  5. washThe organic phase was washed with dilute hydrochloric acid, aqueous sodium bicarbonate solution and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customThe residue was chromatographed on silica gel with 1:1 benzene
  9. customethyl acetate to afford pure product which
  10. customcrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-a1d924139ccd48bb93b241266541c4ba
출처 데이터셋
uspto-grants-1976_12
특허 번호
US04000154

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