| Identification | More | [Name]
N-Cbz-D-Serine | [CAS]
6081-61-4 | [Synonyms]
BENZYLOXYCARBONYL-D-SERINE
CBZ-D-SER-OH
N-ALPHA-CARBOBENZOXY-D-SERINE
N-ALPHA-CBZ-D-SERINE
N-BENZYLOXYCARBONYL-D-SERINE
N-CARBOBENZOXY-D-SERINE
N-CBZ-D-SERINE
Z-D-SERINE
Z-D-SER-OH
N-Benzyloxycarbonyl-D-serine,98+%
CBZ-D-SERINE
N-(Carbobenzyloxy)-D-serine
Z-D-SERINE extrapure
(2R)-2-(Benzyloxycarbonylamino)-3-hydroxypropionic acid
(R)-2-[[(Benzyloxy)carbonyl]amino]-3-hydroxypropinic acid
(R)-3-Hydroxy-2-(benzyloxycarbonylamino)propionic acid | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C11H13NO5 | [MDL Number]
MFCD00063144 | [Molecular Weight]
239.22 | [MOL File]
6081-61-4.mol |
| Chemical Properties | Back Directory | [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. ]
Store at RT. | [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 Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [HS Code ]
2924297099 |
| Hazard Information | Back Directory | [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 |
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