Dimethylformamide → HCID 86734330、化合物

HRID 1974180ノート

反応式

HRID 1974180 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-toluenesulfonyloxymethyl-azetidine, 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 to 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 to 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-137fa34509014590ad82dc1a2a6130eb
出典データセット
uspto-grants-1976_12
特許番号
US04000154

反応ノート

読み込み中…