Acetamidomalonic acid diethyl ester → HCID 21251139, compound

HRID 1532031Notes

Reaction equation

HRID 1532031 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:23][C:24]1[C:25]([O:53][CH2:54][CH3:55])=[N:26][O:27][C:28]=1[C:29]1[N:33]=[CH:32][N:31]([C:34]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:30]=1>CN1CCCC1=O>[C:1]([NH:4][C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH2:23][C:24]1[C:25]([O:53][CH2:54][CH3:55])=[N:26][O:27][C:28]=1[C:29]1[N:33]=[CH:32][N:31]([C:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:30]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 21251151HCID 21251151, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21251139HCID 21251139, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A mixture of diethyl acetamidomalonate (1.3 g, 6.0 mmol) and potassium tert-butoxide (0.73 g, 6.5 mmol) in N-methylpyrrolidone (30 mL) was stirred at room temperature for 30 min. 3-[4-(Bromomethyl)-3-ethoxyisoxazol-5-yl]-1-trityl-1H-1,2,4-triazole (2.8 g, 5.4 mmol) in N-methylpyrrolidone (20 mL) was added (temp 22-28° C.) and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was poured onto an ice/water mixture (250 mL) and the aqueous phase was extracted with EtOAc (3×250 mL). The organic extracts were washed with an aqueous solution of potassium tert-butoxide and brine, dried (Na2SO4) and concentrated in vacuo. Flash chromatography (silica gel, eluent: EtOAc/heptane/triethylamine=50:50:2) gave the title compound (2.2 g, 62%): mp 145-149° C.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 h
  2. extractionthe aqueous phase was extracted with EtOAc (3×250 mL)
  3. washThe organic extracts were washed with an aqueous solution of potassium tert-butoxide and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b56b68ea58494432be2f4d25475af11c
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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