Methyl chloroacetate → N-[3-(2-Methoxyethoxy)phenyl]glycine methyl ester

HRID 1493622Notes

Reaction equation

HRID 1493622 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=[O:4].Cl.[CH3:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(=O)([O-])O.[Na+]>>[CH3:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([NH:16][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 7295Methyl chloroacetateHCID 516892Sodium BicarbonateHCID 16640685131770-50-8

Product 1

HCID 87029700N-[3-(2-Methoxyethoxy)phenyl]glycine methyl esterYield 98.3%

Procedure

Methyl chloroacetate (6.2 ml, 70.3 mmol), the free base of Intermediate 51 (7.84 g, 46.9 mmol) and sodium hydrogencarbonate (7.9 g 93.8 mmol) were heated at 100° C. for 24 h. The reaction was cooled, extracted with ethyl acetate, washed with water, 2N hydrochloric acid and brine, dried (K2CO3) and evaporated to give the title compound (Intermediate 52; 11.03 g, 98%) as a brown oil.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with water, 2N hydrochloric acid and brine
  4. dry with materialdried (K2CO3)
  5. customevaporated

Sources & evidence

ORD record
ord-b55b3d3764684e3a8b54a5dd3713145b
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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