N-Boc-L-tert-Leucine Chemical Properties

Melting point:

118-121 °C

alpha 

-4.2 º (c=1% in glacial acetic acid)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Crystalline Powder

color 

White to slightly yellow

optical activity

[α]20/D 4.2±0.5°, c = 1% in glacial acetic acid

BRN 

1962763

Major Application

peptide synthesis

InChI

InChI=1/C11H21NO4/c1-10(2,3)7(8(13)14)12-9(15)16-11(4,5)6/h7H,1-6H3,(H,12,15)(H,13,14)/t7-/s3

InChIKey

LRFZIPCTFBPFLX-SSDOTTSWSA-N

SMILES

[C@@H](C(=O)O)(C(C)(C)C)NC(=O)OC(C)(C)C |&1:0,r|

CAS DataBase Reference

62965-35-9(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

2924 19 00

HazardClass 

IRRITANT

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

N-Boc-L-tert-Leucine Usage And Synthesis

Description

N-Boc-L-tert-Leucine is a white to slightly yellow crystalline powder. The carboxyl group in its structure can be condensed with alcohol compounds under the catalysis of acid or base to obtain the corresponding ester derivatives. This substance can be used for the synthesis of amino acid drugs due to the various chemical transformation properties of its amine and carboxyl groups. The Boc protective group is able to protect the amino group of the amino acid from non-specific reactions with other reactants. This compound is a derivative of L-tert-Leucine, which is a non-polar amino acid. Its tert-butyl group exhibits significant hydrophobicity and steric hindrance, enabling effective control of molecular conformation in chemical reactions, leading to the formation of chiral compounds. As a crucial chiral intermediate, L-tert-leucine is widely employed in the synthesis of anti-cancer, anti-viral, and biological inhibitors. Additionally, L-tert-leucine serves as an essential additive in the food and cosmetic industry.

Chemical Properties

White crystalline powder

Uses

Atazanavir Related Compound A

reaction suitability

reaction type: Boc solid-phase peptide synthesis
reaction type: C-H Activation
reagent type: ligand
reaction type: Peptide Synthesis

Synthesis

Step A: Synthesis of N-Boc-L-tert-Leucine 1. add triethylamine (56mL, 0.4mol) to a methanol (150mL) suspension of L-tert-leucine (26.1g, 0.2mol) at 0°C. 2. slowly add di-tert-butyl dicarbonate (48g, 0.22mol) to a methanol (40mL) solution of N-Boc-L-tert-leucine. 2. a solution of di-tert-butyl dicarbonate (48 g, 0.22 mol) in methanol (40 mL) was added slowly to the above mixture, controlling the reaction temperature between 0 and 5°C. 3. The reaction mixture was stirred at room temperature overnight. 4. Upon completion of the reaction, the solvent was removed under vacuum. 5. The residue was dissolved in ethyl acetate (200 mL) and the organic layer was washed with 10% w/v aqueous citric acid (3 x 100 mL). 6. The organic layer was dried with anhydrous magnesium sulfate, filtered and the solvent was removed in vacuum to afford N-Boc-L-tert-leucine as a light yellow oil (48.9 g, yield >100% with residual solvent). Product characterization: 1H NMR (CDCl3): δ/ppm 9.20 (1H, bs, NH), 5.10 (1H, m, CH), 4.15 (1H, m, CH), 1.45 (9H, s, tert-butyl in Boc), 1.00 (9H, s, tert-butyl in tert-leucine).

References

[1] Patent: US6716878, 2004, B1. Location in patent: Page column 14
[2] Patent: US6716878, 2004, B1. Location in patent: Page column 62
[3] Patent: CN107325025, 2017, A. Location in patent: Paragraph 0086; 0087
[4] Patent: WO2005/73195, 2005, A2. Location in patent: Page/Page column 96-97
[5] Tetrahedron, 2008, vol. 64, # 18, p. 3980 - 3997

N-Boc-L-tert-Leucine(62965-35-9)Related Product Information

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