Methyl 4-methoxyacetoacetate → HCID 178494554, compound

HRID 2105226Notes

Reaction equation

HRID 2105226 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].S(O)(O)(=O)=O.[CH:16]1([C:19]2[CH:23]=[C:22]([CH:24]3[CH2:28][CH2:27][CH2:26][N:25]3[C:29](=[NH:31])[NH2:30])[O:21][N:20]=2)[CH2:18][CH2:17]1.C[O:33][CH2:34][C:35](=O)[CH2:36][C:37]([O:39][CH3:40])=O>C1COCC1.CO>[CH:16]1([C:19]2[CH:23]=[C:22]([CH:24]3[CH2:28][CH2:27][CH2:26][N:25]3[C:29]3[N:30]=[C:34]([OH:33])[CH:35]=[C:36]([CH2:37][O:39][CH3:40])[N:31]=3)[O:21][N:20]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 123500Methyl 4-methoxyacetoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86047615HCID 86047615, compound

Product 1

HCID 178494554HCID 178494554, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium bis-(trimethylsilyl)amide (3.65 ml of a 2M solution in THF, 7.3 mmol) was added to a solution of 2-(3-cyclopropylisoxazol-5-yl)pyrrolidine-1-carboximidamide mono sulphate (Method 17) (1.83 g, 6.09 mmol) and methyl 4-methoxyacetoacetate (0.867 ml, 6.7 mmol) in methanol (30 ml) and the mixture heated at reflux for 4 hours. The solvent was removed by evaporation and the residue purified by chromatography on silica gel eluting with DCM/Methanol (100:0 increasing in polarity to 95:5). The purified product was triturated with ether and the solid then recrystallised from methanol to give the title compound (565 mg, 29%) as white solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was removed by evaporation
  4. customthe residue purified by chromatography on silica gel eluting with DCM/Methanol (100:0 increasing in polarity to 95:5)
  5. customThe purified product was triturated with ether
  6. customthe solid then recrystallised from methanol

Sources & evidence

ORD record
ord-511694b7a7e94e748428bcd8c6d689ff
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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