DL-4-Methoxyphenylglycine synthesis

11synthesis methods

Product Name:DL-4-Methoxyphenylglycine
CAS Number:22094-69-5
Molecular formula:C9H11NO3
Molecular Weight:181.19

50845-77-7 Synthesis

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Yield:22094-69-5 84%

Reaction Conditions:

Stage #1: DL-4-methoxyphenylglycine ethyl esterwith lithium hydroxide monohydrate;sodium hydroxide in tetrahydrofuran;ethanol at 40; for 3 h;
Stage #2: with phosphoric acid in tetrahydrofuran;ethanol;lithium hydroxide monohydrate; pH=3;

Steps:

K.ii Step (ii): 2-((4-Methoxyphenyl)amino)acetic acid (18)

2M NaOH (aq.) (149 mL, 0.30 mol) was added dropwise to a stirred solution of ethyl 2-((4-methoxyphenyl)amino)acetate (17) (59.2 g, 0.28 mol) in EtOH/THF (300 mU80 mL). The reaction was stirred at 40°C for 3h. The mixture was diluted with water (100 mL) and phosphoric acid (85 % wt in water) (35.9 g, 0.31 mol) was added to pH 3. The resulting brown precipitate was collected by filtration and washed with water (100 mL) and dried under vacuum to give 2-((4-methoxyphenyl)amino)acetic acid (18) (45.5 g, 84 %) as a brown solid: m/z 182 (M+H)⁺ (ES⁺); 180 (M-H)^- (ES^-). ¹H NMR (400 MHz, DMSO-d₆) δ: 6.78-6.64 (m, 2H), 6.55-6.44 (m, 2H), 3.74 (s, 2H), 3.64 (s, 3H).

References:

EP2602248,2013,A1 Location in patent:Paragraph 0162

104-94-9 Synthesis