2-Amino-2,3-dimethylbutanamide → HCID 67643449, compound

HRID 1494558Notes

Reaction equation

HRID 1494558 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][N:6]([CH3:9])[CH:5]1[C:10]1[CH:11]=[C:12]([C:20]([O:22]C)=[O:21])[C:13]([C:16](OC)=O)=[N:14][CH:15]=1)(=[O:3])[CH3:2].[NH2:24][C:25]([CH3:32])([CH:29]([CH3:31])[CH3:30])[C:26]([NH2:28])=[O:27].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[NH4+:4].[C:1]([N:4]1[CH2:8][CH2:7][N:6]([CH3:9])[CH:5]1[C:10]1[CH:15]=[N:14][C:13]([C:16]2[NH:28][C:26](=[O:27])[C:25]([CH:29]([CH3:31])[CH3:30])([CH3:32])[N:24]=2)=[C:12]([CH:11]=1)[C:20]([O-:22])=[O:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 97937732-Amino-2,3-dimethylbutanamideHCID 15672406HCID 15672406, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67643449HCID 67643449, compoundYield 213.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of dimethyl 5-(1-acetyl-3-methyl-2-imidazolidinyl)pyridine-2,3-dicarboxylate (0.70 g, 0.0022 mol), and 2-amino-2,3dimethylbutyramide (0.28 g, 0.0022 mol) in toluene (10 mL) is added potassium tert-butoxide (0.49 g, 0.0044 mol). The resulting mixture is stirred for 2 hours at 80° C. to 90° C. After cooling to room temperature, the reaction is quenched by the addition of water (15 mL) and ammonium chloride (0.25 g). The layers are separated, the aqueous solution concentrated under high vacumn, the product triturated with 33% ethanol in chloroform and filtered. The filtrate is concentrated in vacuo to afford the title compound (0.95 g, 100%) as a gold solid, mp 93°-98° C., identified by IR and NMR spectral analyses.

Workup

  1. customthe reaction is quenched by the addition of water (15 mL) and ammonium chloride (0.25 g)
  2. customThe layers are separated
  3. concentrationthe aqueous solution concentrated under high vacumn
  4. customthe product triturated with 33% ethanol in chloroform
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-cc04aac8c91840409a914aedb64c64f7
Source dataset
uspto-grants-1991_06
Patent number
US05026859

Reaction notes

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