Boc-L-aspartic acid 4-benzyl ester Chemical Properties

Melting point:

98-102 °C(lit.)

alpha 

-20 º (c=2, DMF)

Boiling point:

461.82°C (rough estimate)

Density 

1.1728 (rough estimate)

refractive index 

-20 ° (C=2, DMF)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

almost transparency in N,N-DMF

pka

3.65±0.23(Predicted)

form 

Powder

color 

White to off-white

optical activity

[α]20/D 20.0±1°, c = 2% in DMF

BRN 

2064127

InChI

InChI=1S/C16H21NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-13(18)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1

InChIKey

SOHLZANWVLCPHK-LBPRGKRZSA-N

SMILES

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

CAS DataBase Reference

7536-58-5(CAS DataBase Reference)

EPA Substance Registry System

N-tert-Butoxycarbonyl-L-aspartic acid .beta.-benzyl ester (7536-58-5)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:Boc-L-aspartic acid 4-benzyl ester
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Boc-L-aspartic acid 4-benzyl ester Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

N-?[(1,?1-?Dimethylethoxy)?carbonyl]?-?L-?Aspartic acid 4-?(Phenylmethyl) Ester is L-Aspartic Acid (A790024) with side chain and N-terminus protected. L-Aspartic Acid is a non-essential amino acid found in food sources.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of (S)-4-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid from di-tert-butyl dicarbonate and L-aspartic acid-4-benzyl ester is as follows: in a round-bottomed flask, L-aspartic acid-4-benzyl ester (79.7 g, 357 mmol), sodium bicarbonate (60 g, 714.2 mmol), water (700 mL), and tetrahydrofuran (550 mL). The reaction system was cooled to 0 °C, followed by the slow addition of di-tert-butyl dicarbonate (105 g, 481 mmol) to the reaction vial. After the dropwise addition, the reaction was kept at 0 °C for half an hour, then slowly warmed up to room temperature and continued stirring for 12 hours. After completion of the reaction, tetrahydrofuran was removed by distillation under reduced pressure. The aqueous phase was washed with ethyl acetate (20 mL), followed by adjusting the pH with 10% aqueous citric acid (10 mL) to 1. The aqueous phase was extracted with ethyl acetate (200 mL x 2) and the organic phases were combined. The organic phase was washed sequentially with saturated saline (100 mL × 2) and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give a white solid product (104 g, 90% yield).

References

[1] Patent: CN106866502, 2017, A. Location in patent: Paragraph 0230-0234
[2] Organic Syntheses, 1985, vol. 63, p. 160 - 160
[3] Tetrahedron Letters, 1991, vol. 32, # 45, p. 6637 - 6640
[4] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6541 - 6548
[5] Journal of the American Chemical Society, 2004, vol. 126, # 42, p. 13612 - 13613

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