4-Methylmorpholine → Benzyl 4-(4-fluorophenyl)-2,5-dioxooxazolidine-3-carboxylate

HRID 1801894ノート

反応式

HRID 1801894 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:13])[O:11][C:10](=[O:14])[NH:9]2)=[CH:4][CH:3]=1.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].CN1CCOCC1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:12](=[O:13])[O:11][C:10](=[O:14])[N:9]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 10387Benzyl chloroformateHCID 866490494-(4-Fluorophenyl)oxazolidine-2,5-dione

生成物 1

HCID 11438888Benzyl 4-(4-fluorophenyl)-2,5-dioxooxazolidine-3-carboxylate収率 64.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-(4-fluorophenyl)oxazolidine-2,5-dione (2.5 g, 12.8 mmol) in THF (30 mL) cooled to −25° C. was added benzyl chloroformate (2.3 mL, 16.6 mmol), followed by the slow addition (˜10 min) of N-methylmorpholine (2.11 mL, 19.2 mmol) as a solution in THF (5 mL). The solution was stirred at this temperature for 1 h. and then allowed to warm to rt overnight. The resulting solution was filtered through Celite, and the filtrate was concentrated. The resulting crude material was recrystallized from 2:2:1 t-butyl methyl ether:hexanes:THF to give benzyl 4-(4-fluorophenyl)-2,5-dioxooxazolidine-3-carboxylate (2.7 g, 64%) which was used without further purification.

後処理

  1. filtrationThe resulting solution was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting crude material was recrystallized from 2:2:1 t-butyl methyl ether

出典と根拠

ORDレコード
ord-e731dca2b1424bfd97a0ba00d116f60d
出典データセット
uspto-grants-2013_01
特許番号
US08349851B2

反応ノート

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