Ethanol → HCID 66603916, compound

HRID 2358940Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.S(Cl)(Cl)=O.[CH2:22](O)[CH3:23]>N#N>[CH2:22]([O:16][C:15](=[O:17])[C@H:13]([CH2:12][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[NH2:14])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred slurry of DL-3-(8-hydroxyquinolin-5-yl)alanine (HLM8) (2.19 g, 7.04 mmol) in absolute ethanol (26 ml) at 0° C., with protection from atmospheric moisture by CaCl2 tube in N2, thionyl chloride was added dropwise (1.1 ml, 14.1 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature for 30 minutes, and then refluxed overnight. The solution was evaporated to dryness in vacuum. The residue was dissolved in absolute ethanol and reevaporated to dryness. To ensure completeness of the esterification, the whole operation was repeated. The ester HLM9 (yellow solid, 1.67 g, 92% yield), which was shown by HPLC to contain about 1% of free amino acid, was further purified by FC(CH2Cl2:MeOH:AcOH 9:1.5:1.5). 1H NMR (250 MHz, D2O) 0.94 (dd, J=7.2, 7.2 Hz, 3H), 3.63 (m, 2H), 4.01 (m, 2H), 4.34 (dd, J=7.7, 7.5 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.56 (d, J=8.2 Hz, 1H), 8.01 (dd, J=8.7, 5.4 Hz, 1H), 8.93 (d, J=5.4 Hz, 1H), 9.08 (d, J=8.7 Hz, 1H).

Workup

temperaturerefluxed overnight
customThe solution was evaporated to dryness in vacuum
dissolutionThe residue was dissolved in absolute ethanol
customreevaporated to dryness
customwas further purified by FC(CH2Cl2:MeOH:AcOH 9:1.5:1.5)

Sources & evidence

ORD record: ord-e459a2e7196146c0b480b13ad27c7f8a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685955B2

Reaction notes

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