Pyridine → (5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-[(methanesulfonyl)methyl]-oxazolidin-2-one

HRID 1452579노트

반응식

HRID 1452579 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19]O)[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[N:11][C:10]([CH3:13])=[N:9]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].N1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][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]=[N:11][C:10]([CH3:13])=[N:9]1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2회HCID 57526987(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one2회

생성물 1

HCID 68877351(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-[(methanesulfonyl)methyl]-oxazolidin-2-one수율 44.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one (Intermediate 25) (10.08 g, 34.5 mmol) in dichloromethane (100 ml) and triethylamine (6.0 ml, 43 mmol) was cooled to 0° C. and methanesulfonyl chloride (3.2 ml, 41 mmol) was added by syringe. The reaction mixture was allowed to warm to room temperature overnight. More pyridine (50 ml) was added and the reaction mixture was cooled to 0° C. before adding additional methanesulfonyl chloride (3.2 ml, 41 mmol). The reaction was allowed to warm to room temperature and the solid was collected by filtration and washed with ethyl acetate to afford the crude title compound (5.49 g).

후처리

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. filtrationthe solid was collected by filtration
  4. washwashed with ethyl acetate

출처 및 근거

ORD 기록
ord-56a5d0a3af874a2ba8c508fd039e0ee9
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473699B2

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