m-Chloroperbenzoic acid → diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

HRID 232213ノート

反応式

HRID 232213 の反応式
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:16]3([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])[CH:20](SC4C=CC=CC=4)[CH2:19][C:18](=[O:28])[O:17]3)[C:12]2=[O:45])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:16]3([C:29]([O:31][CH:32]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:30])[CH:20]=[CH:19][C:18](=[O:28])[O:17]3)[C:12]2=[O:45])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 67902355diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-3-phenylthio-2-tetrahydrofurancarboxylate

生成物 1

HCID 67902310diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate収率 42.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In 3 ml of dichloromethane was dissolved 60 mg of the Compound (50) obtained in Example 50. To the solution was added 20 mg of 3-chloroperbenzoic acid. The mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water, successively, followed by drying (Na2SO4). The solvent was then evaporated off, and the residue was dissolved in 1 ml of toluene. The solution was heated at 80° C. for 30 minutes, then the solvent was evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 21 mg of the subject Compound (51) as colorless crystals. The IR and NMR spectra of this product were in agreement with those of the compound obtained in (a) above.

後処理

  1. washThe reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water
  2. dry with materialby drying (Na2SO4)
  3. customThe solvent was then evaporated off
  4. dissolutionthe residue was dissolved in 1 ml of toluene
  5. temperatureThe solution was heated at 80° C. for 30 minutes
  6. customthe solvent was evaporated off
  7. washfollowed by elution with hexane-ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-410a2bb376a44cf1963afbf52657a90a
出典データセット
uspto-grants-1989_07
特許番号
US04851422

反応ノート

読み込み中…