Tetrabutylammonium Fluoride → Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate

HRID 927924노트

반응식

HRID 927924 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][O:39][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]>C1COCC1>[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][OH:39])=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 90071968Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate2회

생성물 1

HCID 70984627Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate수율 60.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Tetrabutylammonium fluoride (1M solution in THF, 1.1 mL) was added to a stirred, cooled solution of methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate (Intermediate 34, 0.43 g) in THF (10 mL) at 0° C. and the mixture was stirred at 0° C. for 40 minutes then evaporated to dryness. The residue was partitioned between ethyl acetate and water and the organic layer was washed with brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-2% to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate (0.2 g) as a gum.

후처리

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-2%

출처 및 근거

ORD 기록
ord-a1a9d103046141fd823563acadee9fe4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

반응 노트

불러오는 중…