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

HRID 232212ノート

反応式

HRID 232212 の反応式
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][NH:13][C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:18]1([C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:22]=[CH:21][C:20](=[O:23])[O:19]1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:18]3([C:24]([O:26][CH:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[O:25])[CH:22]=[CH:21][C:20](=[O:23])[O:19]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 20030875HCID 20030875、化合物HCID 56633768(4S)-4-phenylacetamido-3-isoxazolidinone

生成物 1

HCID 67902310diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate収率 71.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In 2.5 ml of dichloromethane suspension of 35 mg of (4S)-4-phenylacetamido-3-isoxazolidinone and 50 mg of diphenylmethyl 2-chloro-5-oxo-2,5-dihydro-2-furancarboxylate obtained in Example 49 was added under ice-cooling and stirring, 0.025 ml of triethylamine. The reaction solution was stirred at room temperature for 30 minutes, which was diluted with ethyl acetate, followed by washed with water and drying (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 56 mg of the subject Compound (51) as colorless crystals. Recryslallization from dichloromethaneethylether afforded colorless prisms, m.p. 168°-169° C. (decomp.).

後処理

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringThe reaction solution was stirred at room temperature for 30 minutes
  4. washby washed with water
  5. dry with materialdrying (Na2SO4)
  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-b1f80655838d4e0d9bc9002039614732
出典データセット
uspto-grants-1989_07
特許番号
US04851422

反応ノート

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