Triethylamine → Methanesulfonic acid (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester

HRID 723808노트

반응식

HRID 723808 반응식
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][OH:19])[O:15][C:14]3=[O:20])=[CH:9][C:8]=2[F:21])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[S:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][O:19][S:30]([CH3:29])(=[O:32])=[O:31])[O:15][C:14]3=[O:20])=[CH:9][C:8]=2[F:21])[CH2:5][CH2:6]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11335852(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-hydroxymethyloxazolidin-2-one

생성물 1

HCID 11395090Methanesulfonic acid (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-20 °C

실험 절차

(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-hydroxymethyloxazolidin-2-one (14 g, 45.3 mmol) was dissolved in dichloromethane (300 ml) and triethylamine (8.8 ml, 63.3 mmol) was added. It was cooled to −20° C. and methanesulfonyl chloride (4.22 ml, 54.4 mmol), dissolved in dichloromethane (50 ml), was added dropwise. The reaction mixture was allowed to warm to room temperature and was quenched with potassium phosphate buffer (pH 7). Dichloromethane was removed under vacuum and it was extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The title compound (16.9 g) was precipitated from dichloromethane by addition of hexane.

후처리

  1. additionwas added dropwise
  2. temperatureto warm to room temperature
  3. customwas quenched with potassium phosphate buffer (pH 7)
  4. customDichloromethane was removed under vacuum and it
  5. extractionwas extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customThe title compound (16.9 g) was precipitated from dichloromethane by addition of hexane

출처 및 근거

ORD 기록
ord-ab0b6dcec3c44320b58878133e35cee9
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141583B2

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