Boc-L-aspartic acid 4-tert-butyl ester Chemical Properties

Melting point:

64-67 °C

alpha 

2 º (c=1% in MeOH)

Boiling point:

432.6±40.0 °C(Predicted)

Density 

1.139±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in methanol and dimethyl sulfoxide.

form 

Powder

pka

3.69±0.23(Predicted)

color 

White

optical activity

[α]20/D +2.0±0.4°, c = 1% in methanol

BRN 

2336144

InChI

InChI=1S/C13H23NO6/c1-12(2,3)19-9(15)7-8(10(16)17)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,16,17)/t8-/m0/s1

InChIKey

PHJDCONJXLIIPW-QMMMGPOBSA-N

SMILES

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

CAS DataBase Reference

1676-90-0(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

Boc-L-aspartic acid 4-tert-butyl ester Usage And Synthesis

Uses

It is used in the preparation of highly selective thrombin inhibitors. Also used in the preparation of thiopeptides and thioacylating agents.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

2.1. Preparation of Boc-Asp(O-tBu)-NCA (II-a) The method involves the main chain cyclization of a free carboxylic acid in which the amine functional group is protected by Boc. First, (Boc)2-Asp(Ot-Bu)-OH (VII-a) needs to be prepared. The specific steps are as follows: 1. esterify the α-carboxylic acid of Boc-Asp(Ot-Bu)-OH (Va) to benzyl ester (VI-a). 2. reaction with Boc2O in the presence of DMAP to give the bis-Boc-protected amino compound (VII-a). 3. removal of the benzyl ester protecting group by hydrogenation to give (VIII-a). Subsequent steps include cyclization with Vilsmeier salt protected amino acid (VIII-a). The optimum reaction conditions were in acetonitrile with the salt formed from DMF and oxalyl chloride. The final compound (II-a) was obtained in 90% yield.

References

[1] Patent: US2010/16631, 2010, A1. Location in patent: Page/Page column 5-6
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4975 - 4978
[3] Patent: WO2017/24009, 2017, A1. Location in patent: Paragraph 0652
[4] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 5, p. 283 - 287
[5] Bioorganicheskaya Khimiya, 1999, vol. 25, # 5, p. 323 - 328

Boc-L-aspartic acid 4-tert-butyl ester(1676-90-0)Related Product Information

• BUTYL OLEATE
• Cyhalofop-butyl
• N-Boc-L-valine
• tert-Butanol
• Tris(trimethylsilyl)phosphate
• tert-Butyl peroxyacetate
• Diethylene glycol monobutyl ether
• Buprofezin
• Boc-Aib-OH
• Poly-L-aspartic acid
• Fmoc-Lys(Boc)-OH
• L-ASPARTIC ACID
• Butyl acetate
• BOC-GLY-LEU-OH
• BOC-D-2-PYRIDYLALANINE
• N-tert-Butoxycarbonyl-L-glutamic acid gamma-tert-butyl ester
• Boc-L-glutamic acid 5-cyclohexyl ester
• BOC-ORN-OH