Pyridine → HCID 123624177, compound

HRID 718159Notes

Reaction equation

HRID 718159 reaction equation
Cl.[CH3:2][CH:3]([CH3:10])[CH2:4][C:5](=[NH:9])[O:6][CH2:7][CH3:8].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)Cl.CCOC(C)=O>[CH2:21]([O:20][C:18]([N:9]=[C:5]([O:6][CH2:7][CH3:8])[CH2:4][CH:3]([CH3:10])[CH3:2])=[O:19])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 71755542HCID 71755542, compound

Product 1

HCID 123624177HCID 123624177, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-methylbutanimidate hydrochloride (4.0 g, 24.2 mmol) was suspended in DCM (48 mL) and the mixture was cooled to 0° C. Pyridine (10.0 mL, 124 mmol) was added and the mixture was stirred for 15 minutes. Ethyl chloroformate (5.3 mL, 48.3 mmol) was added and the solution was allowed to warm to RT and stirred for 12 h. The mixture was diluted with a mixture of EtOAc and hexanes (1:1, 200 mL) and solids were removed by filtration through a diatomaceous earth. The filtrate was concentrated in vacuo to afford ethyl N-ethoxycarbonyl-3-methyl-butanimidate (4.3 g, 88%) as a colorless viscous oil. 1H NMR (400 MHz, DMSO-d6): δ 4.09 (q, J=7.1 Hz, 2H), 4.05 (q, J=7.1 Hz, 2H), 2.18 (d, J=7.4 Hz, 2H), 1.95-1.94 (m, 1H), 1.20 (t, J=7.1 Hz, 3H), 1.19 (t, J=7.1 Hz, 3H), 0.86 (d, J=6.7 Hz, 6H).

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 12 h
  3. customwere removed by filtration through a diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a3e2dc032f2648a6992dbfc30ea0516d
Source dataset
uspto-grants-2015_11
Patent number
US09193719B2

Reaction notes

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