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 870948Notes

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-6b8e6a965a5a4d479ed15a2312d31117
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969564B2

Reaction notes

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