Water → Carbamic acid, N-[(1S)-1-[[(9-bromo-5-oxo-5H-[1]benzopyrano[3,4-c]pyridin-8-yl)oxy]methyl]-3-methylbutyl]-, 1,1-dimethylethyl ester

HRID 2369538노트

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HRID 2369538 반응식
[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[O:17][C:15]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:38])C(=O)C1.O>C(#N)C>[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:9][O:10][C:11]1[C:12]([Br:38])=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[O:17][C:15]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 86724438HCID 86724438, 화합물

생성물 1

HCID 86724437Carbamic acid, N-[(1S)-1-[[(9-bromo-5-oxo-5H-[1]benzopyrano[3,4-c]pyridin-8-yl)oxy]methyl]-3-methylbutyl]-, 1,1-dimethylethyl ester수율 67.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To a stirred solution of (S)-tert-butyl(4-methyl-1-((5-oxo-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)carbamate (0.100 g, 0.242 mmol) (prepared as described in Example 11, Part E) in anhydrous acetonitrile (2 mL) was added NBS (0.043 g, 0.242 mmol) and the mixture heated to 80° C. for 12 h. After completion of reaction, water (10 mL) was added and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford crude compound which was purified by preparative TLC to afford (S)-tert-butyl(1-((9-bromo-5-oxo-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (80 mg, 0.163 mmol, 67% yield) as a pale yellow solid. LCMS (ESI) m/e 491.2 [(M+H)+, calcd for C23H28BrN2O5491.1] LC/MS retention time (method F): tR=1.12 min.

후처리

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude compound which
  6. customwas purified by preparative TLC

출처 및 근거

ORD 기록
ord-c6db6ccf1dcc47ef9d0f67a5e3d35742
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703953B2

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