2,6-Lutidine → 5-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-1h-pyrrole-2-carboxylic acid methyl ester

HRID 639867노트

반응식

HRID 639867 반응식
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]([CH:20]1[C:24]([CH3:25])=[CH:23][C:22](=O)[N:21]1C(OC(C)(C)C)=O)=[O:19].N1C(C)=CC=CC=1C>ClCCl>[CH3:16][O:17][C:18]([C:20]1[NH:21][C:22]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:23][C:24]=1[CH3:25])=[O:19]

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 575874573-Methyl-5-oxo-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 575874385-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-1h-pyrrole-2-carboxylic acid methyl ester수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

tert-Butyldimethylsilyltrifluoromethanesulfonate (9.99 ml, 11.49 g, 43.5 mmol, 3.0 equiv) was added to a stirring solution of 3-methyl-5-oxo-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.7 g, 14.5 mmol, 1.0 equiv) and 2,6-lutidine (5.07 ml, 4.66 g, 43.5 mmol, 3.0 equiv) in dichloromethane (100 ml) at 23° C. The mixture was stirred at 23° C. for 15 h, then washed with pH=7 buffer solution (30 ml). The aqueous layer was extracted with two 40 ml portions of dichloromethane. The combined organic layers were dried over sodium sulfate. The solids were filtered and the filtrate was concentrated. The residue was purified by flash column chromatography (3% ethyl acetate-hexanes initially, grading to 6% ethyl acetate-hexanes) to afford 5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-1H-pyrrole-2-carboxylic acid methyl ester (3.46 g, 89%) as a yellow oil.

후처리

  1. washwashed with pH=7 buffer solution (30 ml)
  2. extractionThe aqueous layer was extracted with two 40 ml portions of dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash column chromatography (3% ethyl acetate-hexanes initially

출처 및 근거

ORD 기록
ord-0fdd89974f2640a0a6d1785b7ce98db8
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691896B2

반응 노트

불러오는 중…