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

HRID 2050386

反応式

HRID 2050386 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-0368cccc862944fc9927d83d24ce23d7
出典データセット
uspto-grants-1980_04
特許番号
US04200572

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