N-Cbz-D-Serine

N-Cbz-D-Serine Property

Melting point:

116-119°C

Boiling point:

487.5±45.0 °C(Predicted)

Density 

1.354±0.06 g/cm3(Predicted)

refractive index 

-6 ° (C=6, AcOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetic Acid (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.60±0.10(Predicted)

color 

Off-White

BRN 

2058313

InChI

InChI=1S/C11H13NO5/c13-6-9(10(14)15)12-11(16)17-7-8-4-2-1-3-5-8/h1-5,9,13H,6-7H2,(H,12,16)(H,14,15)/t9-/m1/s1

InChIKey

GNIDSOFZAKMQAO-SECBINFHSA-N

SMILES

C(O)(=O)[C@@H](CO)NC(OCC1=CC=CC=C1)=O

CAS DataBase Reference

6081-61-4(CAS DataBase Reference)

Safety

Safety Statements 

22-24/25

HS Code 

2924297099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

N-Cbz-D-Serine Chemical Properties,Usage,Production

Uses

N-Benzyloxycarbonyl-D-serine is D-serine (S270975) with amine protected from eletrophiles by carboxybenzyl group in organic synthesis. N-Benzyloxycarbonyl-D-serine can be used to synthesize acetamido-methoxypropionamides such as Desacetyl Desmethyl Lacosamide (D288325) which is a potent anticonvulsant.

Synthesis

GENERAL STEPS: Dissolve sodium bicarbonate (605 g, 5.72 mol) in water (3 L) and cool to 0-5°C in an ice bath. D-serine (200 g, 1.90 mol) was added in 8-10 portions, 20-30 minutes apart. Subsequently, a toluene solution of 50% benzyl chloroformate (780 g, 2.29 mol) was added slowly and dropwise over a period of 1 h. The temperature was maintained at 0-5°C. The reaction mixture was stirred at 0-5 °C for 2 h, then brought to room temperature and continued stirring for 2 h. The reaction was carried out at room temperature. Ethyl acetate (400 mL) was added and the pH was adjusted with hydrochloric acid to 2.0. The product was extracted with ethyl acetate (2 x 800 mL). The organic phases were combined and concentrated under reduced pressure to about 640 mL to give a suspension. Cyclohexane (1200 mL) was added and slurried for 6 hours. The purified product was collected by filtration and dried under reduced pressure at 50 °C to afford (R)-2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoic acid (432.5 g, 95% yield) as a white solid with a melting point of 119-120 °C (literature value of 119 °C) and [α]D25 -5.08 (c 2.7, acetic acid).IR (ν, cm-1 ): 1689 (C=O) 1749 (C=O), 3319 (NH), 3338 (OH).UV (λmax, nm): 208.1H NMR (CD3OD, δ, ppm, J/Hz): 3.83-3.92 (2H, m, CH2), 4.30 (1H, t, J=8.8, NCH), 5.13 (2H, s, CH2), 7.29- 7.40 (5H, m, Ph-H).13C NMR (CD3OD, δ, ppm): 57.7, 63.1, 67.7, 128.9 (2C), 129.0, 129.5 (2C), 138.1, 158.6, 173.8.Mass Spectrometry (m/z, Irel%): 238 [M-H]- (100).

References

[1] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3114 - 3116
[2] Chemistry of Heterocyclic Compounds, 2017, vol. 53, # 11, p. 1248 - 1253
[3] Khim. Geterotsikl. Soedin., 2017, vol. 53, # 11, p. 1248 - 1253,6
[4] European Journal of Organic Chemistry, 2001, # 16, p. 3067 - 3074
[5] Asian Journal of Chemistry, 2011, vol. 23, # 11, p. 5169 - 5170