Hydrochloric Acid → (5R)-3-(4-Ethynyl-3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 1371833ノート

反応式

HRID 1371833 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[N:21]3)[O:16][C:15]2=[O:26])[CH:5]=[CH:6][C:7]=1[C:8]#[C:9][Si](C)(C)C.[OH-].[K+].Cl>CO>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[N:21]3)[O:16][C:15]2=[O:26])=[CH:3][C:2]=1[F:1])#[CH:9]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58626908(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one2 回

生成物 1

HCID 58626911(5R)-3-(4-Ethynyl-3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one収率 80.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

(5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 10, 1.4 g, 3.76 mmol) was dissolved in methanol (10 ml) and cooled to 0° C. 1N potassium hydroxide aqueous solution (4 mL) was added and the mixture was stirred for one hour. 2M HCl (4 mLl) was added and the reaction mixture was stirred for 30 minutes. It was extracted with dichloromethane (30 mL), the organic phase was concentrated to dryness. The product was preciptitated from dichloromethane (10 mL) by the additon of hexanes (50 mL) to give the product as a colourless solid (0.91 g).

後処理

  1. stirringthe reaction mixture was stirred for 30 minutes
  2. extractionIt was extracted with dichloromethane (30 mL)
  3. concentrationthe organic phase was concentrated to dryness

出典と根拠

ORDレコード
ord-b3006ba2b64d4ee5b0cea97b5b5df0f3
出典データセット
uspto-grants-2007_01
特許番号
US07157482B2

反応ノート

読み込み中…