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

HRID 127903

반응식

HRID 127903 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-89f9976778ce48cb908d81aab7fe93fe
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04257947

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