Ethanol → HCID 66603916, compound

HRID 557245Notes

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-9cf2909fde66436e9d70fdbc2ee07eb6
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058442B2

Reaction notes

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