Methyl iodide → HCID 57750353, compound

HRID 423058Notes

Reaction equation

HRID 423058 reaction equation
IC.[C:3]([C@H:10]([CH:14]([NH2:22])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)C(O)=O)([O:5][C:6](C)(C)C)=[O:4].[C:23](=[O:26])([O-])[O-:24].[K+].[K+]>CN(C=O)C>[C:15]([O:24][C:23]([NH:22][C@@H:14]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)[CH2:10][C:3]([O:5][CH3:6])=[O:4])=[O:26])([CH3:20])([CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57350134HCID 57350134, compound

Product 1

HCID 57750353HCID 57750353, compoundYield 199.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Iodomethane (0.987 mL, 15.85 mmol) was added in one portion to boc-(R)-3-amino-3-(4-chloro-phenyl)-propionic acid (950 mg, 3.17 mmol) and potassium carbonate (876 mg, 6.34 mmol) in DMF (15 mL). The resulting suspension was stirred at 80° C. for 24 hours. The reaction mixture was concentrated and diluted with EtOAc (25 mL) with water (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford (R)-methyl 3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoate (990 mg, 100%) as a orange solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc (25 mL) with water (25 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-07a963850d634a7293042e43d8b67b91
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

Loading…