2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(4-cyanophenyl)propanoate

Base Information

• Chemical Name: 2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(4-cyanophenyl)propanoate
• CAS No.: 146727-62-0
• Molecular Formula: C15H18N2O4
• Molecular Weight: 290.319
• Hs Code.: 29223900
• DSSTox Substance ID: DTXSID40932896
• Wikidata: Q72448955
• Mol file: 146727-62-0.mol

Synonyms:DTXSID40932896;A808544;2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(4-cyanophenyl)propanoate;(2R)-2-(tert-butoxycarbonylamino)-3-(4-cyanophenyl)propanoate;N-Boc-4-cyano-D-phenylalanine

Chemical Property of 2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(4-cyanophenyl)propanoate

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Melting Point: 152.6 °C
• Refractive Index: 1.6280 (estimate)
• Boiling Point: 494 °C at 760 mmHg
• PKA: 3.73±0.10(Predicted)
• Flash Point: 252.6 °C
• PSA: 99.42000
• Density: 1.22 g/cm₃
• LogP: 2.46958
• Storage Temp.: -15°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 289.11883203
• Heavy Atom Count: 21
• Complexity: 419

Purity/Quality:

99% ^*data from raw suppliers

Boc-4-cyano-D-phenylalanine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)C#N)C(=O)[O-]
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=C(C=C1)C#N)C(=O)[O-]
• Uses: N-Boc-4-cyano-D-phenylalanine is used as pharmaceutical intermediate.

Technology Process of 2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(4-cyanophenyl)propanoate

There total 4 articles about 2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(4-cyanophenyl)propanoate 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: 100.0%

→ (2R)-2-[(tert-butoxy)carbonylamino]-3-(4-cyanophenyl)propanoic acid (146727-62-0)

Guidance literature:

Reference yield: 96.6%

di-tert-butyl dicarbonate (24424-99-5) + D-(p-cyanophenylalanine) hydrochloride → (2R)-2-[(tert-butoxy)carbonylamino]-3-(4-cyanophenyl)propanoic acid (146727-62-0)

Guidance literature:

With sodium hydroxide; In water; tert-butyl alcohol; at 20 ℃;

DOI:10.1021/jm2011996

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (2R)-2-amino-3-(4-cyanophenyl)propanoic acid (263396-44-7) → (2R)-2-[(tert-butoxy)carbonylamino]-3-(4-cyanophenyl)propanoic acid (146727-62-0)

Guidance literature:

With sodium hydroxide; In water; tert-butyl alcohol; at 20 ℃;

upstream raw materials:

di-tert-butyl dicarbonate

(2R)-2-amino-3-(4-cyanophenyl)propanoic acid

Downstream raw materials:

Boc-D-Phe(4-AMe)-OH*CH₃COOH

Refernces

• 1、 Saupe, Sebastian M.,Steinmetzer, Torsten. "A new strategy for the development of highly potent and selective plasmin inhibitors". supporting information; experimental part. p. 1171 - 1180. Retrieved 2012/04/17.
• 2、 -. "UREA DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE". Page/Page column 64. . Retrieved 2010/11/23.