Triethylamine → (5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate

HRID 1167492

반응식

HRID 1167492 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][OH:20])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][O:20][S:30]([CH3:29])(=[O:32])=[O:31])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21356561(5R)-3-(3-Fluoro-4-(4-methylimidazol-1-yl)phenyl)-5-hydroxymethyloxazolidin-2-one

생성물 1

HCID 21356562(5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate수율 78.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

3-(3-Fluoro-4-(4-methyl-imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (11.8 g, 40.5 mmol) was stirred in a mixture of pyridine (200 ml) and triethylamine (4.86 g, 48.2 mmol) under nitrogen in an ice-bath. Methanesulfonyl chloride (5.16 g, 45 mmol) was added dropwise, and the mixture stirrd for 2 hours, allowing the temperature to rise to ambient. Solvent was evaporated, and the residue stirred vigorously with a mixture of aqueous sodium bicarbonate (5%, 200 ml) and isohexane (200 ml). The precipitate was filtered, washed with water then isohexane, and dried. The residue was recrystallised from hot acetone (200 ml) by dilution with isohexane (300 ml) to give the title product (11.7 g), mp 151-153°. MS (EI): 369 (M+) for C15H16FN3O5S.

후처리

  1. customSolvent was evaporated
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dry with materialisohexane, and dried
  5. customThe residue was recrystallised from hot acetone (200 ml) by dilution with isohexane (300 ml)

출처 및 근거

ORD 기록
ord-93225f4a235d440caf92912ed08e8063
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617339B1

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