Hydrochloric Acid → HCID 178494575, 화합물

HRID 1900058노트

반응식

HRID 1900058 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 178494572HCID 178494572, 화합물

생성물 1

HCID 178494575HCID 178494575, 화합물수율 77.5%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-78eb0a4d99334bf3a0af235f4ac136a0
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574055

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