(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate Chemical Properties

Melting point:

63-64 °C

Boiling point:

507.6±50.0 °C(Predicted)

Density 

1.103±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

pka

10.62±0.46(Predicted)

color 

White to Off-White

(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate Usage And Synthesis

Uses

(R)-tert-Butyl 1-(Benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate is an intermediate in the synthesis of functionalized amino acids, and in the synthesis of antiepileptic drug (R)-lacosamide.

Synthesis

The general procedure for the synthesis of (R)-2-tert-butoxycarbonylamino-N-benzyl-3-methoxypropanamide from tert-butyl (R)-(1-(phenylmethylamino)-3-hydroxy-1-oxopropan-2-yl)carbamate and dimethyl sulfate was as follows: toluene (4.8 L) was added to a reactor at room temperature, followed by the addition of the Lacosamide Phase II product (1 kg) , and the mixture was cooled to 0°C. Sodium hydroxide solution (0.54 kg), tetrabutylammonium bromide (0.186 kg) and dimethyl sulfate (0.86 kg) were added sequentially, and then the reaction mixture was heated to 30°C with continuous stirring for 90 minutes. After completion of the reaction, the organic phase was separated by extraction with toluene and washed by adding 5% sodium bicarbonate solution. Cyclohexane was added to the organic phase and stirred for 10 minutes, followed by concentration under reduced pressure at 50°C for 2 hours. Finally, the product was dried to give lacosamide III in about 96.28% yield.

References

[1] Patent: CN106957239, 2017, A. Location in patent: Paragraph 0036; 0045-0047
[2] Patent: EP2399901, 2011, A1. Location in patent: Page/Page column 8
[3] Patent: US2011/319649, 2011, A1. Location in patent: Page/Page column 5
[4] Patent: US2011/34731, 2011, A1. Location in patent: Page/Page column 7
[5] Patent: WO2011/144983, 2011, A2. Location in patent: Page/Page column 26-27

(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate(880468-89-3)Related Product Information

• (R)-2-(4-BROMOPHENYL)PYRROLIDINE HCl
• (R)-3,3,3-TRIFLUORO-2-HYDROXY-2-METHYLPROPIONIC ACID
• Lacosamide
• Desmethyl Lacosamide
• N-DescarboxyMethyl-N-carboxyethyl LacosaMide (IMpurity)
• Desacetyl DesMethyl LacosaMide
• LacosaMide iMpurity
• LacosaMide (raceMate)
• Lacosamide
• (S)-2-Acetamido-N-benzyl-3-methoxypropanamide
• 2-(Acetylamino)-N-(phenylmethyl)-2-propenamide
• (R)-O-Acetyl-LacosaMide
• LACOSAMIDE
• Benzylamine hydrochloride
• N-Desacetyl Lacosamide HCl salt