N-BOC-O-Benzyl-L-serine Chemical Properties

Melting point:

58-60 °C(lit.)

alpha 

21.5 º (c=2, ethanol)

Boiling point:

437.02°C (rough estimate)

Density 

1.1454 (rough estimate)

refractive index 

22 ° (C=2, EtOH)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Solid

pka

3.53±0.10(Predicted)

color 

White to Almost white

optical activity

[α]20/D +20±1°, c = 2% in ethanol: water (4:1)

BRN 

3064461

InChIKey

DMBKPDOAQVGTST-LBPRGKRZSA-N

CAS DataBase Reference

23680-31-1(CAS DataBase Reference)

EPA Substance Registry System

N-tert-Butoxycarbonyl-O-benzyl-L-serine (23680-31-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:N-(tert-Butoxycarbonyl)-O-benzyl-L-serine

N-BOC-O-Benzyl-L-serine Usage And Synthesis

Chemical Properties

White powder

Uses

N-Boc-O-benzyl-L-serine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Example 36 Synthesis of N-tert-butoxycarbonyl-O-benzyl-L-serine 39: Boc-L-serine (15 g, 73.09 mmol) was dissolved in DMF (300 mL) at 0 °C, NaH (6.43 g, 160.80 mmol, 60% mineral oil dispersion) was slowly added, and the reaction temperature was maintained at 0 °C and stirred for 1.5 hours. Subsequently, benzyl bromide (13.75 g, 80.40 mmol) was added, and the reaction mixture was gradually warmed to room temperature and continued to stir overnight. Upon completion of the reaction, DMF was removed by evaporation under reduced pressure and the residue was dissolved in H2O. The crude product was partitioned between water and Et2O. The aqueous phase was acidified with 3N HCl to pH < 4 and then extracted three times with EtOAc. The EtOAc extracts were combined, washed with H2O, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give N-tert-butoxycarbonyl-O-benzyl-L-serine (17.27 g, 80% yield).

References

[1] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3225 - 3229
[2] Patent: US2004/121316, 2004, A1
[3] Patent: US2005/239054, 2005, A1
[4] Patent: WO2014/120783, 2014, A1. Location in patent: Paragraph 00145
[5] Patent: WO2018/26763, 2018, A1. Location in patent: Page/Page column 81

N-BOC-O-Benzyl-L-serine(23680-31-1)Related Product Information

• BOC-D-Alanine
• D-Cycloserine
• tert-Butanol
• Benzyl bromide
• DL-Serine
• Benzyl chloride
• tert-Butyl carbazate
• PYRAZOPHOS
• Benzyl alcohol
• L-Homoserine
• L-ALPHA-PHOSPHATIDYLSERINES, BRAIN, BOVINE
• Boc-Ser(tBu)-OH
• L-Serine
• N-Carbobenzyloxyglycine
• CARBONYL SULFIDE
• Benzyl benzoate
• Boc-D-Ser(Bzl)-OH
• Boc-His(Trt)-OH