Dimethylformamide → HCID 66939757, compound

HRID 1364180Notes

Reaction equation

HRID 1364180 reaction equation
[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].[H-].[Na+].BrC[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([O:21][CH3:22])=[O:20].[CH3:23]N(C=O)C>>[CH3:22][O:21][C:19](=[O:20])[C:14]1[CH:13]=[CH:18][CH:17]=[C:16]([CH2:23][N:5]2[C:6](=[O:7])[CH2:8][N:2]([CH3:1])[C:3]2=[O:4])[CH:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 692171-MethylhydantoinHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 66939757HCID 66939757, compound

Conditions

Temperature
0 °C

Procedure

To methylhydantoine (50 mg, 0.438 mmol) in DMF (2 mL) is added at 0° C. sodium hydride (23 mg, 0.525 mmol). After stirring at 0° C. during 1 h, methyl 2-bromomethylphenylcarboxylate (121 mg, 0.525 mmol) is added and the mixture is stirred at rt during 2 h before quenching with an aqueous saturated NaHCO3 solution and DCM. The organic phase is dried and evaporated to give a crude compound before purification by preparative HPLC (Column Waters C18 ODB 5 μm 19×50, Gradient: 0-2.5 min 5% ACN, 2.5-12.5 min 5-100% ACN, 12.5-15 min 100% ACN) to yield the title compound.

Workup

  1. stirringthe mixture is stirred at rt during 2 h
  2. custombefore quenching with an aqueous saturated NaHCO3 solution and DCM
  3. customThe organic phase is dried
  4. customevaporated
  5. customto give a crude compound
  6. custombefore purification by preparative HPLC (Column Waters C18 ODB 5 μm 19×50, Gradient: 0-2.5 min 5% ACN, 2.5-12.5 min 5-100% ACN, 12.5-15 min 100% ACN)

Sources & evidence

ORD record
ord-eb07aa7258444edda3dca6268f969e85
Source dataset
uspto-grants-2011_02
Patent number
US07888351B2

Reaction notes

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