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 1371833노트

반응식

HRID 1371833 반응식
[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]

참가 물질

5

반응물 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-one2회

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-b3006ba2b64d4ee5b0cea97b5b5df0f3
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157482B2

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