2,6-Lutidine → p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 2291002

反応式

HRID 2291002 の反応式
[CH2:1]([S:3][CH:4]1[N:7]([CH:8](O)[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH2:5]1)[CH3:2].CC1C=CC=C(C)N=1.S(Cl)([Cl:34])=O>O1CCCC1>[CH2:1]([S:3][CH:4]1[N:7]([CH:8]([Cl:34])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH2:5]1)[CH3:2]

参加物

5

反応物 3

HCID 79372,6-LutidineHCID 24386Thionyl ChlorideHCID 14050377p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

生成物 1

HCID 14050378p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 6.8 g. of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate in 200 ml. of tetrahydrofuran, at 0°-5° C., was added 2.98 ml. of 2,6-dimethylpyridine, followed by dropwise addition of a solution of 1.73 ml. of thionyl chloride in 20 ml. of tetrahydrofuran, over a 5-minute period. Stirring was continued at 0°-5° C. for 15 minutes, and then the reaction mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was dissolved in 200 ml. of dichloromethane. The resulting solution was washed successively with dilute hydrochloric acid and water, and then dried over anhydrous sodium sulfate. Evaporation in vacuo gave 7.12 g of the title compound as a yellow, viscous liquid. The IR spectrum chloroform of the product showed an absorption at 5.63 microns. The NMR spectrum deuterochloroform of the product showed peaks at 1.3 (t, 3H); 2.47-3.7 (m, 4H); 4.9-5.3 (m, 1H); 5.4 (s, 4H); 6.06 and 6.18 (ss, 1H); 7.58 (d, 2H); and 8.22 (d, 2H) ppm.

後処理

  1. filtrationthe reaction mixture was filtered
  2. customThe filtrate was evaporated to dryness in vacuo
  3. dissolutionthe residue was dissolved in 200 ml
  4. washThe resulting solution was washed successively with dilute hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation in vacuo

出典と根拠

ORDレコード
ord-4094fd8c3b144bd0984760f509810317
出典データセット
uspto-grants-1986_10
特許番号
US04619783

関連ノート

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