Dichloromethane → HCID 54076724, compound

HRID 1765988Notes

Reaction equation

HRID 1765988 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:17])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][CH3:16])[CH:9]=1)[NH2:6].ClCCl.C(=O)([O-])[O-].[K+].[K+].[Cl:27][CH2:28][C:29](Cl)=[O:30]>O>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([NH:6][C:29](=[O:30])[CH2:28][Cl:27])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][CH3:16])[CH:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 69331780HCID 69331780, compound

Product 1

HCID 54076724HCID 54076724, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-methoxy-4-methyl-D-phenylalanine methyl ester hydrochloride (1.60 g) in a mixed solvent of dichloromethane (7 ml) and water (9 ml) was added potassium carbonate (1.70 g) in small portions under ice cooling. Chloroacetyl chloride (0.66 ml) was added to the mixture at 5° C. or below over 15 minutes and then the total mixture was stirred for 30 minutes. The organic layer was separated, washed with an aqueous sodium chloride solution, dried over magnesium sulfate and the solvent was evaporated under reduced pressure to give (2R)-2-[N-(chloroacetyl)amino]-3-(3-methoxy-4-methylphenyl)propionic acid methyl ester in the form of an oily substance.

Workup

  1. customThe organic layer was separated
  2. washwashed with an aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-712ce4f3e4514dda9ff178e7cb72e4ba
Source dataset
uspto-grants-2007_06
Patent number
US07229992B2

Reaction notes

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