Water → Butyl cis-3-azido-4-oxo-2-azetidinecarboxylate

HRID 127903

反応式

HRID 127903 の反応式
C([N:14]1[C:17](=[O:18])[C@H:16]([N:19]=[N+:20]=[N-:21])[C@@H:15]1[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])(C1C=CC=CC=1)C1C=CC=CC=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].O.O.O.O.O.O.O.O.O.O.O.O.P(O)([O-])([O-])=O.[Na+].[Na+].O>C(#N)C>[N:19]([C@H:16]1[C:17](=[O:18])[NH:14][C@H:15]1[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])=[N+:20]=[N-:21]

参加物

6

反応物 4

HCID 962WaterHCID 24412Potassium PersulfateHCID 61456Phosphoric acid, disodium salt, dodecahydrateHCID 86735452Butyl cis-1-benzhydryl-3-azido-4-oxo-2-azetidine carboxylate

生成物 1

HCID 86735451Butyl cis-3-azido-4-oxo-2-azetidinecarboxylate収率 175.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 200 mg (0.529 mmole) of butyl cis-1-benzhydryl-3-azido-4-oxo-2-azetidine carboxylate, 473 mg (1.75 mmole) of potassium persulfate, 307 mg (0.858 mmole) of disodium phosphate dodecahydrate, 9.2 ml of water and 8.4 ml of acetonitrile was thoroughly degassed with argon and then heated to 80°-85° C. under argon for three hours. The reaction mixture was cooled and the acetonitrile removed on the rotary evaporator. The aqueous residue was saturated with solid sodium chloride and extracted three times with ethyl acetate. The combined organic extractions were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 197 mg of crude material. This material was chromatographed on ten grams of 70-230 mesh silica gel and 31 mg (28%) of the desired product, a light yellow foam was eluted with 20% EtOAc in benzene. tlc: silica gel GF; 20% ethylacetate benzene, R.f.=0.15.

後処理

  1. customwas thoroughly degassed with argon
  2. temperatureheated to 80°-85° C. under argon for three hours
  3. temperatureThe reaction mixture was cooled
  4. customthe acetonitrile removed on the rotary evaporator
  5. extractionextracted three times with ethyl acetate
  6. extractionThe combined organic extractions
  7. washwere washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-89f9976778ce48cb908d81aab7fe93fe
出典データセット
uspto-grants-1981_03
特許番号
US04257947

関連ノート

読み込み中…