Dimethylformamide → HCID 86734330、化合物

HRID 2050384ノート

反応式

HRID 2050384 の反応式
[O:1]=[C:2]1[NH:5][C@@H:4]([CH2:6]OS(C2C=CC(C)=CC=2)(=O)=O)[C@H:3]1[NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[N-:29]=[N+:30]=[N-:31].[Na+].CN(C)C=O.C(OCC)(=O)C>C(Cl)Cl>[N:29]([CH2:6][C@H:4]1[C@@H:3]([NH:18][C:19](=[O:28])[CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:2](=[O:1])[NH:5]1)=[N+:30]=[N-:31]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86734329cis-4-Oxo-3-phenoxyacetylamino-2-p-toluenesulfonyloxymethylazetidine

生成物 1

HCID 86734330HCID 86734330、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture containing 1.131 g (2.8 mmole) of cis-4-oxo-3-phenoxyacetylamino-2-p-toluenesulfonyloxymethylazetidine, 0.961 g (14.8 mmole) of sodium azide and 25 ml of anhydrous N,N-dimethylformamide was heated under argon at 40° for 6 hours then at ambient temperature for 24 hours. The reaction mixture was poured into ethyl acetate and was washed with water. The combined aqueous washes were extracted once with ethyl acetate and the ethyl acetate fractions were combined and extracted with brine. After drying the ethyl acetate solution (MgSO4) and filtering, the solvent was removed in vacuo to afford a yellow semi-crystalline residue. This residue was slurried in methylene dichloride and chromatographed on 25 g of silica gel (70-230 mesh). The 1:1 ethyl acetate:methylene dichloride fractions afforded the title compound; tlc: ethyl acetate, silica gel GF, Rf=0.38; mp 142°-143° (dec) (ethyl acetate-hexane).

後処理

  1. temperaturewas heated under argon at 40° for 6 hours
  2. washwas washed with water
  3. extractionThe combined aqueous washes were extracted once with ethyl acetate
  4. extractionextracted with brine
  5. dry with materialAfter drying the ethyl acetate solution (MgSO4)
  6. filtrationfiltering
  7. customthe solvent was removed in vacuo
  8. customto afford a yellow semi-crystalline residue
  9. customchromatographed on 25 g of silica gel (70-230 mesh)

出典と根拠

ORDレコード
ord-66b9d575e9214c049119088834dba16b
出典データセット
uspto-grants-1980_04
特許番号
US04200572

反応ノート

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