(4-METHOXY-BENZOYLAMINO)-ACETIC ACID Chemical Properties

Melting point:

155-158°

Boiling point:

463.7±30.0 °C(Predicted)

Density 

1.268±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.53±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HazardClass 

IRRITANT

(4-METHOXY-BENZOYLAMINO)-ACETIC ACID Usage And Synthesis

Definition

ChEBI: 2-[(4-methoxyphenyl)formamido]acetic acid is a N-acylglycine. It is functionally related to a N-benzoylglycine.

Synthesis

General procedure for the synthesis of 2-(4-methoxybenzoylamino)acetic acid from compound (CAS:51220-57-6): the synthesis of compound g was carried out when R1 was methoxyphenyl. The procedure was as follows: 4-methoxybenzoic acid a (2.00 g, 13.80 mmol) was added to a 200 mL round-bottomed flask with 60 mL of dichloromethane (DCM), followed by the sequential addition of EDCI (13.80 mmol), HOBt (13.80 mmol), compound b (15.77 mmol), and triethylamine (Et3N 45.99 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, it was washed sequentially with water, saturated ammonium chloride solution and saturated brine and the organic phase was dried with anhydrous sodium sulfate. Purification by column chromatography with an eluent ratio of petroleum ether:ethyl acetate = 5:1 to 2:1 afforded compound c (1.80 g, 62.7% yield). Subsequently, compound c was added directly to a mixture containing 45 mL of methanol and 45 mL of aqueous sodium hydroxide (15.19 mmol) and heated to reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was evaporated. After adding a small amount of water, the mixture was transferred to a beaker and the pH was adjusted to 1-2 with concentrated hydrochloric acid. extracted with ethyl acetate (EA), the organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated to give a white solid d (1.22 g, 76.5% yield).

References

[1] Organic Letters, 2016, vol. 18, # 4, p. 696 - 699
[2] Patent: CN107216282, 2017, A. Location in patent: Paragraph 0060; 0061; 0062; 0063; 0064

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