2-Amino-2,3-dimethylbutanamide → HCID 15672411, compound

HRID 1974464Notes

Reaction equation

HRID 1974464 reaction equation
[O:1]1[CH2:7][CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:8]1[CH:9]=[C:10]([C:18]([O:20]C)=[O:19])[C:11]([C:14](OC)=O)=[N:12][CH:13]=1.[NH2:22][C:23]([CH3:30])([CH:27]([CH3:29])[CH3:28])[C:24]([NH2:26])=[O:25].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.O>[O:3]1[CH2:4][CH2:5][CH2:6][CH2:7][O:1][CH:2]1[C:8]1[CH:13]=[N:12][C:11]([C:14]2[NH:26][C:24](=[O:25])[C:23]([CH:27]([CH3:29])[CH3:28])([CH3:30])[N:22]=2)=[C:10]([CH:9]=1)[C:18]([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 97937732-Amino-2,3-dimethylbutanamideHCID 15672403HCID 15672403, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15672411HCID 15672411, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

5-(1,3-Dioxepan-2-yl)-2,3-pyridinedicarboxylic acid, dimethyl ester (0.9 g, 0.00305 mol) in toluene is added to 2-amino-2,3-dimethylbutyramide (0.4 g, 0.00305 mol) and potassium tert-butoxide (0.69 g, 0.0061 mol) in toluene. The mixture is heated for 3 hours from 60° to 70° C. The reaction mixture is cooled to room temperature, water is added and the mixture is concentrated in vacuo to give an oil. The oil is diluted with water and washed with ether. The aqueous solution is acidified to pH 3.1 with 2 normal hydrochloric acid solution and extracted with methylene chloride. The combined methylene chloride extracts are dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound as a white solid (0.63 g, 57%) mp 60°-69° C., identified by IR and NMR spectral analyses.

Workup

  1. temperatureThe mixture is heated for 3 hours from 60° to 70° C
  2. concentrationthe mixture is concentrated in vacuo
  3. customto give an oil
  4. washwashed with ether
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined methylene chloride extracts are dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-372e46479efc4fa5ae869639b7c4d073
Source dataset
uspto-grants-1994_02
Patent number
US05283230

Reaction notes

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