Water → Rac-(3-chloro-4-methanesulfonyl-phenyl)-(cyclohex-2-enyloxy)-acetic acid methyl ester

HRID 1019212노트

반응식

HRID 1019212 반응식
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)=[N+]=[N-].[OH2:19]>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)[O:19][CH:12]1[CH2:11][CH2:10][CH2:9][CH:8]=[CH:7]1

참가 물질

5

반응물 2

HCID 962WaterHCID 86584876(3-Chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester

생성물 1

HCID 67484566Rac-(3-chloro-4-methanesulfonyl-phenyl)-(cyclohex-2-enyloxy)-acetic acid methyl ester수율 58%

시약·촉매·용매 2

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
25 °C

실험 절차

A solution of (3-chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester (Example 6; 489 mg, 1.69 mmol) in dichloromethane (10 mL) at 25° C. was treated with 2-cyclohexen-1I-ol (0.42 mL, 4.23 mmol) followed by rhodium (11) acetate dimer (15 mg, 0.034 mmol) and the resulting solution was stirred at 25° C. for 1 h. The reaction mixture was diluted with dichloromethane (10 mL), then was poured into water (15 mL) and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography (Biotage Flash 40S column, 75/25 hexanes/ethyl acetate) provided rac-(3-chloro-4-methanesulfonyl-phenyl)-(cyclohex-2-enyloxy)-acetic acid methyl ester (350 mg, 58% yield) as a colorless oil: EI-HRMS m/e calcd for C16H19ClS O5 (M+) 358.0642, found 358.0640.

후처리

  1. extractionextracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by chromatography (Biotage Flash 40S column, 75/25 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-74a258cd4a3e4442bf484bf3ce216801
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486184B2

반응 노트

불러오는 중…