Methyl iodide → HCID 66608460, compound

HRID 1529549Notes

Reaction equation

HRID 1529549 reaction equation
IC.[C:3]([O:7][C:8]([N:10]1[CH2:17][C:16]2[O:15][C:14]([C:18]([OH:20])=[O:19])=[N:13][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:21]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:21][O:19][C:18]([C:14]1[O:15][C:16]2[CH2:17][N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[CH2:11][C:12]=2[N:13]=1)=[O:20]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66614583HCID 66614583, compound

Product 1

HCID 66608460HCID 66608460, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Iodomethane (0.098 mL, 1.58 mmol) was added to a stirred solution of 4,6-dihydro-pyrrolo[3,4-d]oxazole-2,5-dicarboxylic acid 5-tert-butyl ester (0.10 g, 0.39 mmol) and K2CO3 (0.10 g, 0.78 mmol) in DMF (2 mL). The mixture was stirred at 100° C. for 5 minutes under microwave irradiation, diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 4,6-dihydro-5H-pyrrolo[3,4-d]oxazole-2,5-dicarboxylic acid 5-(1,1-dimethylethyl) 2-methyl ester (0.055 g, 96% yield) as a pale yellow solid that was used in the next step without further purification. C12H16N2O5 LCMS: Rt 2.31, m/z 269 [M+H]+ (using method, LC-MS Method 4).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-72cac6ded00841c7aa63654ad630e3cb
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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