Dimethyl 2,2-dimethyl-3-oxobutanedioate → HCID 178500133, compound

HRID 1505463Notes

Reaction equation

HRID 1505463 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11](=[NH:14])[NH:12][NH2:13])=[N:9][N:8]([CH2:15][C:16]3[C:21]([F:22])=[CH:20][CH:19]=[C:18]([F:23])[C:17]=3[F:24])[C:5]2=[N:6][CH:7]=1.[CH3:25][C:26]([CH3:37])([C:31](=O)[C:32](OC)=[O:33])[C:27]([O:29][CH3:30])=[O:28]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]=[N:13][C:31]([C:26]([CH3:37])([CH3:25])[C:27]([O:29][CH3:30])=[O:28])=[C:32]([OH:33])[N:14]=3)=[N:9][N:8]([CH2:15][C:16]3[C:21]([F:22])=[CH:20][CH:19]=[C:18]([F:23])[C:17]=3[F:24])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 85519062Dimethyl 2,2-dimethyl-3-oxobutanedioateHCID 178512738HCID 178512738, compound

Product 1

HCID 178500133HCID 178500133, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

6.85 g (20.271 mmol) of the compound from Example 81A were dissolved in 300 ml of ethanol, 7.629 g (40.542 mmol) of dimethyl 2,2-dimethyl-3-oxobutanedioate (described in J. Am. Chem. Soc. 124(14), 3680-3691; 2002) were added and the mixture was stirred at 50° C. overnight. After cooling, a precipitate was filtered off and washed with ethanol. The filtrate was concentrated and then purified by preparative HPLC (methanol:water-75:25). This gave 3.30 g (33% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationa precipitate was filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. custompurified by preparative HPLC (methanol:water-75:25)

Sources & evidence

ORD record
ord-43830502429148899a49ef7277b62b34
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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