DL-4-Methoxyphenylglycine synthesis
- Product Name:DL-4-Methoxyphenylglycine
- CAS Number:22094-69-5
- Molecular formula:C9H11NO3
- Molecular Weight:181.19
![ethyl 2-[(4-methoxyphenyl)amino]acetate](/CAS/20150408/GIF/50845-77-7.gif)
50845-77-7
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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
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![methyl 2-[(4-methoxyphenyl)amino]acetate](/CAS/20180906/GIF/147749-35-7.gif)
147749-35-7
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22094-69-5
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