Sodium Carbonate → HCID 89668435, 화합물

HRID 1482210노트

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HRID 1482210 반응식
[C:1](Cl)(=[O:17])[O:2][CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15].[CH2:19]([S:21][S:22][CH2:23][C@H:24]([NH:28][CH3:29])[C:25]([OH:27])=[O:26])[CH3:20].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>O1CCOCC1.O>[CH3:13][O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:4]([CH2:3][O:2][C:1]([N:28]([CH3:29])[C@@H:24]([CH2:23][S:22][S:21][CH2:19][CH3:20])[C:25]([OH:27])=[O:26])=[O:17])=[C:5]([N+:14]([O-:16])=[O:15])[CH:6]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 3084878((Nitroveratryl)oxy)chlorocarbamateHCID 89668341HCID 89668341, 화합물2회

생성물 1

HCID 89668435HCID 89668435, 화합물수율 93.4%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

4,5-Dimethoxy-2-nitrobenzyl carbonochloridate (394 mg, 1.43 mmol) was added to a solution of (R)-3-(ethyldisulfanyl)-2-(methylamino)propanoic acid (Compound 2f-F) (232 mg, 1.19 mmol) and sodium carbonate (252 mg, 2.38 mmol) in dioxane (3 ml) and water (3 ml), and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution (3 ml) was added to the reaction mixture, after which the mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic extract was then dried over magnesium sulfate. Following concentration under reduced pressure, the resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100) to afford (R)-2-((((4,5-dimethoxy-2-nitrobenzyl)oxy)carbonyl)(methyl)amino)-3-(ethyldisulfanyl)propanoic acid (Compound 2k-F) (483 mg, 93%).

후처리

  1. extractionafter which the mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. extractionThe organic extract
  4. dry with materialwas then dried over magnesium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100)

출처 및 근거

ORD 기록
ord-e891292b2bab4a0bb7d0738c4f2ed099
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409952B2

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