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 870948ノート

反応式

HRID 870948 の反応式
[CH3:1][CH:2]([CH3:30])[CH2:3][C@H:4]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:20]3[C:15](=[CH:16][N:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[O:13][C:11]=2[CH:12]=1.C1C(=O)N([Br:38])C(=O)C1.O>C(#N)C>[Br:38][C:8]1[C:7]([O:6][CH2:5][C@@H:4]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH:2]([CH3:30])[CH3:1])=[CH:12][C:11]2[O:13][C:14](=[O:21])[C:15]3[C:20]([C:10]=2[CH:9]=1)=[CH:19][CH:18]=[N:17][CH:16]=3

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 86724438HCID 86724438、化合物

生成物 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 ester収率 67.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6b8e6a965a5a4d479ed15a2312d31117
出典データセット
uspto-grants-2015_03
特許番号
US08969564B2

反応ノート

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