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

HRID 723808ノート

反応式

HRID 723808 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-20 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-ab0b6dcec3c44320b58878133e35cee9
出典データセット
uspto-grants-2006_11
特許番号
US07141583B2

反応ノート

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