benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate Chemical Properties

Melting point:

150 - 151°C

Boiling point:

818.2±65.0 °C(Predicted)

Density 

1.137±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Heated)

pka

11.22±0.46(Predicted)

form 

Solid

color 

White to Off-White

InChIKey

AKIABKDAWVWIHO-DPQUEHIJNA-N

SMILES

[C@H](C(=O)OCC1C=CC=CC=1)(NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)OC(C)(C)C)CCC1C=CC=CC=1)CC1C=CC=CC=1 |&1:0,14,22,r|

benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate Usage And Synthesis

Uses

(αS)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzenebutanoyl-L-leucyl-phenylmethyl Ester L-Phenylalanine is used as a reagent in the preparation of peptides for inhibition of enzymes.

Synthesis

Example 2: Preparation of Compound of Formula VII 1. Cool a mixture of dichloromethane (90 mL) and trifluoroacetic acid (210 mL) to 2-6 °C and add the compound of Formula IV (100 g, 1 eq.) at 37 °C. Maintain the same temperature. 2. The reaction mixture was heated to 25-30 °C and stirred at this temperature for 2 hours. 3. Add dichloromethane (1.5 L) to the reaction mixture, adjust the pH to 7-8 with 25% sodium carbonate solution at 20-30 °C and stir for 20 min at the same temperature. 4. The organic layer was separated and washed sequentially with water (300 mL) and 10% sodium chloride solution (300 mL). 5. Separate the organic layer and concentrate under vacuum at less than 35°C to obtain a residue. 6. The resulting residue was dissolved in dimethylformamide (500 mL) and cooled to 2-6°C. 7. 7. HOBt (2.9 g, 0.1 eq.), PyBOP (133.5 g, 1.2 eq.), N-Boc-homophenylalanine (59.7 g, 1 eq.) and diisopropylethylamine (110.5 g, 4 eq.) were slowly added to the reaction mixture at 2-6 °C. 8. The reaction mixture was heated to 25-30 °C and stirred at this temperature for 2-3 hours. 9. After completion of the reaction, the reaction mixture was slowly poured into water (5 L) at 25-30 °C and stirred at the same temperature for 2-3 hours. 10. The precipitated solid was filtered, washed with water (500 mL) and dried to afford (αS)-α-[[tert-butoxycarbonyl]amino]phenylbutyryl-L-leucyl-L-phenylalanine benzyl ester. Yield: 130 g; PXRD: Figure 2; DSC: heat-absorption peak at ca. 150 °C; HPLC chemical purity: 99.97%; HOBt: 0.1%, PyBOP: not detected, tris(pyrrolidinylphosphine) oxide: 0.02% by HPLC, respectively.

References

[1] Patent: WO2016/185450, 2016, A1. Location in patent: Page/Page column 61-62

benzyl ((S)-2-((tert-butoxycarbonyl)aMino)-4-phenylbutanoyl)-L-leucyl-L-phenylalaninate(868540-15-2)Related Product Information

• (alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine
• 1-Pentanone, 2-aMino-4-Methyl-1-[(2R)-2-Methyloxiranyl]-, (2S)-, trifluoroacetate (9CI)
• CarbaMic acid, N-[(1S)-3-Methyl-1-[[(2R)-2-Methyl-2-oxiranyl]carbonyl]butyl]-, 1,1-diMethylethyl ester