Basic information Safety Supplier Related

(R)-2-(methoxycarbonylamino)-2-phenylacetic acid

Basic information Safety Supplier Related

(R)-2-(methoxycarbonylamino)-2-phenylacetic acid Basic information

Product Name:
(R)-2-(methoxycarbonylamino)-2-phenylacetic acid
Synonyms:
  • (R)-2-(methoxycarbonylamino)-2-phenylacetic acid
  • (R)-2-(methoxycarbonylamino)-2-phenyl
  • Moc-D-Phg-OH
  • (R)-2-(Methoxycarbonylamino)-2-phenylethanoic acid
  • (alphaR)-alpha-[(Methoxycarbonyl)amino]benzeneacetic acid
  • (2R)-2-[(methoxycarbonyl)amino]-2-phenylacetic acid
  • Moc-D-Phg
  • Benzeneacetic acid, a-[(methoxycarbonyl)amino]-, (aR)-
CAS:
50890-96-5
MF:
C10H11NO4
MW:
209.2
Product Categories:
  • intermediates
Mol File:
50890-96-5.mol
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(R)-2-(methoxycarbonylamino)-2-phenylacetic acid Chemical Properties

Melting point:
120 °C
Boiling point:
391.3±35.0 °C(Predicted)
Density 
1.283±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
form 
powder to crystal
pka
3.96±0.10(Predicted)
color 
White to Almost white
optical activity
Consistent with structure
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(R)-2-(methoxycarbonylamino)-2-phenylacetic acid Usage And Synthesis

Uses

(R)-2-((Methoxycarbonyl)amino)-2-phenylacetic acid is a Glycine.html" class="link-product" target="_blank">Glycine (HY-Y0966) derivative[1].

Synthesis

875-74-1

79-22-1

50890-96-5

D-Phenylglycine (10.0 g, 66.1 mmol) and sodium hydroxide (21.2 g, 265 mmol) were dissolved in water (60 mL) at 0°C and stirred until completely dissolved. Subsequently, methyl chloroformate (10.2 mL, 133 mmol) was added slowly and dropwise over 20 minutes. The reaction mixture was continued to be stirred at 0°C for 1 hour. Upon completion of the reaction, it was acidified with concentrated hydrochloric acid (25 mL, 300 mmol) to pH < 2. The acidic aqueous phase was extracted with ethyl acetate (3 x 100 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration to remove the desiccant, the organic phase was concentrated under reduced pressure to afford N-methoxycarbonyl-D-phenylglycine (Int-2a, 12.6 g, 91% yield), which could be used for subsequent reactions without further purification.

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144. DOI:10.1080/10408398.2012.708368

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