Triethylamine → Ethyl 2-[(benzyloxy)(3-ethoxy-3-oxopropanoyl)amino]nicotinate

HRID 601158Notes

Reaction equation

HRID 601158 reaction equation
[CH2:1]([O:8][NH:9][C:10]1[N:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH:29]([C:35]([O-])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31]>ClCCl>[CH2:1]([O:8][N:9]([C:35](=[O:36])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:10]1[N:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59224790Ethyl 2-[(benzyloxy)amino]nicotinateHCID 86592122Monoethyl chloromalonate

Product 1

HCID 86592121Ethyl 2-[(benzyloxy)(3-ethoxy-3-oxopropanoyl)amino]nicotinateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 157A (1.2 g, 4.4 mmol) and triethylamine (0.49 g, 4.8 mmol) in dichloromethane (25 mL) was treated dropwise with ethyl chloromalonate (0.73 g, 4.8 mmol), stirred for 2 hr and partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by column chromatography on silica gel eluting with hexane and ethyl acetate (3:1) to provide the title compound (1.1 g, 65%). MS (DCI) m/z 387 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customthe layers were separated
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel eluting with hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-efd6d4300000405dacf9ea1030a7a911
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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