BOC-D-4-Nitrophe

Base Information

• Chemical Name: BOC-D-4-Nitrophe
• CAS No.: 61280-75-9
• Molecular Formula: C₁₄H₁₈N₂O₆
• Molecular Weight: 310.307
• Hs Code.: 29242990
• Mol file: 61280-75-9.mol

Synonyms:N-(tert-Butoxycarbonyl)-4-nitro-D-phenylalanine;N-(tert-Butyloxycarbonyl)-p-nitro-D-phenylalanine;N-Boc-p-nitro-D-phenylalanine;Boc-D-Phe(4-NO2)-OH;

Chemical Property of BOC-D-4-Nitrophe

Chemical Property:

• Appearance/Colour: whaite crystalline powder
• Melting Point: 120 °C
• Boiling Point: 509.3 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 261.8 °C
• PSA: 121.45000
• Density: 1.29 g/cm³
• LogP: 3.02930
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-p-nitro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-p-nitro-D-phenylalanine is the N-Boc protected form of p-Nitro-D-phenylalanine (N502720). Also a useful synthetic intermediate in the synthesis of (R)-Hydroxymelphalan (H393845, TFA salt); an analog of Melphalan (M216900) which is an antineoplastic.

Technology Process of BOC-D-4-Nitrophe

There total 4 articles about BOC-D-4-Nitrophe 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: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-4-nitro-phenylalanine (56613-61-7) → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-nitrophenyl)propanoic acid (33305-77-0,86937-80-6,105453-25-6,61280-75-9)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2006.03.021

Reference yield: 86.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + (R)-4-nitro-phenylalanine (56613-61-7) → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-nitrophenyl)propanoic acid (33305-77-0,86937-80-6,105453-25-6,61280-75-9)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 18h;

DOI:10.1016/S0968-0896(97)00130-2

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-nitrophenyl)propanoic acid (33305-77-0,86937-80-6,105453-25-6,61280-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. H₂SO₄; HNO₃ / 1.5 h / 0 - 20 °C

1.2: 16 percent / aq. NH₄OH / 96 h / 4 °C

2.1: 92 percent / aq. NaHCO₃ / dioxane / 24 h / 20 °C

With sulfuric acid; nitric acid; sodium hydrogencarbonate; In 1,4-dioxane;

DOI:10.1016/j.ejmech.2006.03.021

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(R)-4-nitro-phenylalanine

di-tert-butyl dicarbonate

D-(R)-phenylalanine

Downstream raw materials:

N^α-t-BOC-trans-4-aminocyclohexyl-D-alanine

N^α-t-BOC-cis-4-aminocyclohexyl-D-alanine

(R,E)-N-(3-(4-((3,5-bis(trifluoromethyl)phenyl)diazenyl)phenyl)-1-((2-hydroxyphenyl)amino)-1-oxopropan-2-yl)-2-hydroxybenzamide

C₂₂H₂₁N₃O₄

Refernces

• 1、 Sassatelli, Mathieu,Debiton, éric,Aboab, Bettina,Prudhomme, Michelle,Moreau, Pascale. "Synthesis and?antiproliferative activities of?indolin-2-one?derivatives bearing amino acid moieties". . p. 709 - 716. Retrieved 2007/10/03.
• 2、 Rao, Pemmaraju N.,Peterson, Dorothy M.,Acosta, C. Kirk,Bahr, Martin L.,Kim, Hyun K.. "SYNTHESIS OF cis AND trans-4-AMINOCYCLOHEXYL-D-ALANINE DERIVATIVES AND DETERMINATION OF THEIR STEREOCHEMISTRY". . p. 103 - 110. Retrieved 2007/10/03.