Sodium Bicarbonate → Ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate

HRID 1087268

Reaction equation

HRID 1087268 reaction equation
Cl[CH2:2][C:3]1[N:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:16][C@@:17]([C:22]([NH2:24])=[O:23])([CH:19]([CH3:21])[CH3:20])[NH2:18].C(=O)(O)[O-].[Na+]>CS(C)=O>[C:22]([C:17]([NH:18][CH2:2][C:3]1[N:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:16])[CH:19]([CH3:21])[CH3:20])(=[O:23])[NH2:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10154071(S)-2-Amino-2,3-dimethylbutanamideHCID 14600680Ethyl 2-chloromethyl-5-ethylnicotinate

Product 1

HCID 14600682Ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 77 g of ethyl 2-chloromethyl-5-ethylnicotinate (0.338 mol), 44 g of α-methylvalinamide (0.338 mol) and 33.5 g of sodium bicarbonate (0.4 mol) in 60 mL dimethylsulfoxide is stirred and heated at 80° for 16 hours. The reaction is partitioned between 1:1 ethylacetate-hexane and water. The organic layer is washed thoroughly with water, dried, and concentrated in vacuo to a gum. Chromatography of this gum on silica gel using hexane-ethyl acetate mixtures as eluant affords the title product, mp 68°-72°.

Workup

  1. temperatureheated at 80° for 16 hours
  2. customThe reaction is partitioned between 1:1 ethylacetate-hexane and water
  3. washThe organic layer is washed thoroughly with water
  4. customdried
  5. concentrationconcentrated in vacuo to a gum

Sources & evidence

ORD record
ord-e6e687bf94e1470ea7bea9cc5462de5b
Source dataset
uspto-grants-1991_07
Patent number
US05034532

Linked notes

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