Pyridine → HCID 66685209, compound

HRID 409643Notes

Reaction equation

HRID 409643 reaction equation
[CH2:1]([O:6][C:7](=O)[CH:8]([NH:16][C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[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>[CH2:9]([C:8]1[N:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:5]=[C:4]2[CH2:3][CH2:2][CH2:1][O:6][C:7]=12)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 66685066HCID 66685066, compound

Product 1

HCID 66685209HCID 66685209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
15 °C

Procedure

Pent-4-en-1-yl2-(2-ethoxy-2-oxoacetamido)-3-phenylpropanoate (0.80 g, 1 eq) and DCM (15 mL) were added to a vessel with stirring. Pyridine (0.23 g, 1.2 eq) was then added and the mixture was cooled to 15° C. Tf2O (1.0 g, 1.5 eq) was added to the mixture over 15 min and the mixture was warmed to ambient temperature. The solution was stirred for 3.5 h after which time the reaction was quenched by DCM and 20 wt % aqueous NaOAc to form a biphasic mixture. The layers were separated and the organic layer was extracted with 6N HCl (3×10 mL). The combined acid layers were washed with DCM and the pH was adjusted to ˜9 with solid K2CO3. The basic aqueous layer was extracted with DCM. The organic layer was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.74 (s, 1H), 7.10-7.35 (m, 5H), 4.43 (q, J=7.12 Hz, 2H), 4.22-4.29 (m, 2H), 4.21 (s, 2H), 2.78 (t, J=6.41 Hz, 2H), 1.93-2.06 (m, 2H), 1.41 (t, J=7.12 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ ppm 165.08, 152.25, 149.62, 138.86, 138.06, 129.62, 128.61, 127.80, 125.61, 125.23, 66.70, 60.97, 38.55, 23.93, 20.92, 14.10; HRMS (M+H) m/z, calcd for C18H20NO3, 298.1443; found 298.1450.

Workup

  1. temperaturethe mixture was warmed to ambient temperature
  2. stirringThe solution was stirred for 3.5 h after which time the reaction
  3. customwas quenched by DCM and 20 wt % aqueous NaOAc
  4. customto form a biphasic mixture
  5. customThe layers were separated
  6. extractionthe organic layer was extracted with 6N HCl (3×10 mL)
  7. washThe combined acid layers were washed with DCM
  8. extractionThe basic aqueous layer was extracted with DCM
  9. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8840da2259714b2dae8b4c9916acd1fc
Source dataset
uspto-grants-2014_06
Patent number
US08759523B2

Reaction notes

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