Pyridine → HCID 66685727, compound

HRID 409642Notes

Reaction equation

[CH2:1]([O:6][C:7](=O)[CH:8]([NH:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:9])[CH2:2][CH2:3][CH:4]=[CH2:5].N1C=CC=CC=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH3:9][C:8]1[N:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[C:4]2[CH2:3][CH2:2][CH2:1][O:6][C:7]=12

Participants

Conditions

Temperature: 15 °C

Procedure

Pent-4-en-1-yl2-(2-ethoxy-2-oxoacetamido)propanoate (1.05 g, 1 eq) and DCM (15 mL) were added to a vessel with stirring. Pyridine (0.39 g, 1.2 eq) was then added and the mixture was cooled to 15° C. Tf2O (1.7 g, 1.5 eq) was added to the mixture over 15 min and the mixture was warmed to ambient temperature to stir for 1.5 h. The reaction was quenched by the addition of DCM and 20 wt % aqueous NaOAc to form a biphasic mixture. The layers were separated and the organic layer was washed with water. The organic layer was then concentrated under reduced pressure to provide the title compound as yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.62 (s, 1H), 4.32 (q, J=7.12 Hz, 2H), 4.16-4.25 (m, 2H), 2.70 (t, J=6.44 Hz, 2H), 2.37 (s, 3H), 1.86-2.03 (m, 2H), 1.31 (t, J=7.12 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm 165.15, 152.44, 147.98, 137.72, 128.73, 124.80, 66.85, 61.09, 23.98, 21.06, 18.98, 14.11; HRMS (M+H) m/z, calcd for C12H16NO3, 222.1130; found, 222.1133.

Workup

temperaturethe mixture was warmed to ambient temperature
stirringto stir for 1.5 h
customThe reaction was quenched by the addition of DCM and 20 wt % aqueous NaOAc
customto form a biphasic mixture
customThe layers were separated
washthe organic layer was washed with water
concentrationThe organic layer was then concentrated under reduced pressure

Sources & evidence

ORD record: ord-ac5a96ad14c544a2be758067527b6ecb
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759523B2

Reaction notes

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