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50890-96-5

50890-96-5 Structure

50890-96-5 Structure
IdentificationBack Directory
[Name]

(R)-2-(methoxycarbonylamino)-2-phenylacetic acid
[CAS]

50890-96-5
[Synonyms]

Moc-D-Phg
Moc-D-Phg-OH
(R)-2-(methoxycarbonylamino)-2-phenyl
(R)-2-(methoxycarbonylamino)-2-phenylaceticaci
(R)-2-(methoxycarbonylamino)-2-phenylacetic acid
(R)-2-(Methoxycarbonylamino)-2-phenylethanoic acid
(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetic acid
Benzeneacetic acid, a-[(methoxycarbonyl)amino]-, (aR)-
Benzeneacetic acid, α-[(methoxycarbonyl)amino]-, (αR)-
(alphaR)-alpha-[(Methoxycarbonyl)amino]benzeneacetic acid
[Molecular Formula]

C10H11NO4
[MDL Number]

MFCD12796004
[MOL File]

50890-96-5.mol
[Molecular Weight]

209.2
Chemical PropertiesBack Directory
[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 Rotation]

Consistent with structure
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
[REACH Registrations]

Active
Hazard InformationBack Directory
[Uses]

(R)-2-((Methoxycarbonyl)amino)-2-phenylacetic acid is a Glycine (HY-Y0966) derivative[1].
[Synthesis]

D-2-Phenylglycine

875-74-1

Methyl chloroformate

79-22-1

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

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
Spectrum DetailBack Directory
[Spectrum Detail]

(R)-2-(methoxycarbonylamino)-2-phenylacetic acid(50890-96-5)1HNMR
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