N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER

Base Information

• Chemical Name: N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER
• CAS No.: 116366-27-9
• Molecular Formula: C18H26 N2 O6
• Molecular Weight: 366.414
• Mol file: 116366-27-9.mol

Synonyms:N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER

Chemical Property of N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 493.6°Cat760mmHg
• Flash Point: 252.3°C
• PSA: 110.45000
• Density: 1.161g/cm³
• LogP: 4.28640

Purity/Quality:

98.5% ^*data from raw suppliers

N-Boc-4-nitro-L-phenylalaninet-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-4-nitro-L-phenylalanine t-Butyl Ester is a useful synthetic intermediate in the synthesis of (2S)-2-Amino-3-(4-morpholin-4-ylphenyl)propanoic Acid (A618690); an impurity of Melphalan (M216900) which is an antineoplastic.

Technology Process of N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER

There total 6 articles about N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + Boc-Phe(p-NO2)-OH (33305-77-0) → (S)-N-[(tert-butyloxy)carbonyl]-[4-nitrophenyl]alanine tert-butyl ester (116366-27-9)

Guidance literature:

tert-Butyl 2,2,2-trichloroacetimidate; Boc-Phe(p-NO₂)-OH; With boron trifluoride diethyl etherate; In dichloromethane; cyclohexane; at 0 - 20 ℃; for 0.666667h;

With sodium hydrogencarbonate; In dichloromethane; cyclohexane;

Reference yield:

ethyl acetate n-hexane + di-tert-butyl dicarbonate (24424-99-5) + 4-nitro-3-phenyl-L-alanine (949-99-5) + isobutene (115-11-7,15220-85-6) → (S)-N-[(tert-butyloxy)carbonyl]-[4-nitrophenyl]alanine tert-butyl ester (116366-27-9)

Guidance literature:

With triethylamine; In 1,4-dioxane; concentrated H₂ SO₄; water; ethyl acetate;

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (S)-N-[(tert-butyloxy)carbonyl]-[4-nitrophenyl]alanine tert-butyl ester (116366-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 53 percent / HNO₃; H₂SO₄

2: 92 percent / dioxane; H₂O / 24 h / 0 - 20 °C

3: toluene / 0.67 h / 80 °C

With sulfuric acid; nitric acid; In 1,4-dioxane; water; toluene; 1: Nitration / 2: Substitution / 3: Esterification;

DOI:10.1021/jo982161f

upstream raw materials:

di-tert-butyl dicarbonate

Boc-Phe(p-NO₂)-OH

N,N-dimethylformamide di-tert-butyl acetal

L-phenylalanine

Downstream raw materials:

melphalan hydrochloride

(S)-N-[(tert-butyloxy)carbonyl]-[4-thioureaphenyl]alanine tert-butyl ester

L-4-nitrophenylalanine tert-butyl ester

Refernces

• 1、 Atkinson,Moore,Tobin,King. "Asymmetric synthesis of conformationally restricted L-arginine analogues as active site probes of nitric oxide synthase". . p. 3467 - 3475. Retrieved 2007/10/03.
• 2、 Pozdnev, V. F.. "ACTIVATION OF CARBOXYLIC ACIDS WITH PYROCARBONATES. SYNTHESIS OF t-BUTYL ESTERS OF N-PROTECTED AMINO ACIDS FROM DI-t-BUTYL PYROCARBONATE IN THE PRESENCE OF PYRIDINE AND 4-DIMETHYLAMINOPYRIDINE". . p. 592 - 597. Retrieved 2007/10/02.