Hydrochloric Acid → HCID 178494575、化合物

HRID 1900058ノート

反応式

HRID 1900058 の反応式
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]3=[O:22])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C(Cl)Cl.N1C=CC=CC=1>[CH3:21][O:20][CH2:19][CH:17]1[O:16][C:15](=[O:22])[N:14]([C:11]2[CH:10]=[CH:9][C:8]([C@H:5]3[CH2:6][CH2:7][C@H:2]([O:1][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:3][CH2:4]3)=[CH:13][CH:12]=2)[CH2:18]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 178494572HCID 178494572、化合物

生成物 1

HCID 178494575HCID 178494575、化合物収率 77.5%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 0.5 g (1.639 mmol) of (RS)-3-[4-(trans-4-hydroxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one in 20 ml of methylene chloride and 5 ml of pyridine was treated dropwise with a solution of 0.95 ml (8.195 mmol) of benzoyl chloride in 10 ml of methylene chloride and stirred at room temperature for a further 3 hours. The reaction mixture was poured into ice-water, made acid with 3N hydrochloric acid and extracted with methylene chloride. The organic phase was washed with wate, dried over magnesium sulfate and the solvent was distilled off. The benzoate crystallized upon treatment with t-butyl methyl ether. There was obtained 0.52 g (77%) of benzoic acid (RS)-trans-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-cyclohexyl ester. M.p.: 104°-105°.

後処理

  1. extractionextracted with methylene chloride
  2. washThe organic phase was washed with wate
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe benzoate crystallized upon treatment with t-butyl methyl ether

出典と根拠

ORDレコード
ord-78eb0a4d99334bf3a0af235f4ac136a0
出典データセット
uspto-grants-1996_11
特許番号
US05574055

反応ノート

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