Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate → methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate

HRID 927923노트

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HRID 927923 반응식
[C:1]([NH:4][C:5]1[C:14]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[CH2:20][OH:21])=[CH:13][CH:12]=[C:11]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[H][H]>O1CCOCC1.C(O)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([NH:4][C:5]1[C:14]([C@H:15]2[CH2:19][CH2:18][O:17][C@H:16]2[CH2:20][OH:21])=[CH:13][CH:12]=[C:11]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

참가 물질

6

반응물 2

HCID 70984627Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate2회HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 70983847methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate수율 69.3%

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 176Acetic Acid용매HCID 312751,4-Dioxane용매

실험 절차

A solution of methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate (Intermediate 38, 0.2 g) in dioxane (4 mL) and acetic acid (1 mL) was treated under an atmosphere of nitrogen with palladium hydroxide on carbon (10%, 0.03 g). The nitrogen was replaced by hydrogen and the mixture was stirred under an atmosphere of hydrogen overnight. The mixture was filtered through Celite and the pad was washed thoroughly with ethyl acetate. 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 0-10% to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate (0.14 g) as a white solid.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. washthe pad was washed thoroughly with ethyl acetate
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%

출처 및 근거

ORD 기록
ord-4ab099e12fdc4939a777b4c08bdd6a57
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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