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

Base Information

• Chemical Name: 2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(3-fluorophenyl)propanoate
• CAS No.: 114873-01-7
• Molecular Formula: C14H18FNO4
• Molecular Weight: 283.3
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20921521
• Wikidata: Q72449276
• Mol file: 114873-01-7.mol

Synonyms:DTXSID20921521;A803256;2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(3-fluorophenyl)propanoate;(2S)-2-(tert-butoxycarbonylamino)-3-(3-fluorophenyl)propanoate;Boc-Phe(3-F)-OH

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

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 5.57E-08mmHg at 25°C
• Melting Point: 75-80 °C
• Refractive Index: 1.517
• Boiling Point: 425 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 210.8 °C
• PSA: 75.63000
• Density: 1.216 g/cm³
• LogP: 2.73700
• Storage Temp.: Keep Cold
• Solubility.: slightly sol. in Ethanol
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 282.11416119
• Heavy Atom Count: 20
• Complexity: 348

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-3-fluoro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=CC=C1)F)C(=O)[O-]
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)F)C(=O)[O-]

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

There total 8 articles about 2-{[tert-Butoxy(hydroxy)methylidene]amino}-3-(3-fluorophenyl)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%

di-tert-butyl dicarbonate (24424-99-5) + L-3-fluorophenylalanine (19883-77-3,2629-54-1) → N-Boc-3-fluoro-L-phenylalanine (114873-01-7,114873-11-9)

Guidance literature:

di-tert-butyl dicarbonate; L-3-fluorophenylalanine; With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 5h;

With citric acid; In water;

Reference yield: 85.0%

L-3-fluorophenylalanine (19883-77-3,2629-54-1) + tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate → N-Boc-3-fluoro-L-phenylalanine (114873-01-7,114873-11-9)

Guidance literature:

With sodium carbonate; In water; acetonitrile; at 25 ℃; for 12h;

DOI:10.1080/00397911.2017.1366525

Reference yield: 74.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl (S)-2-acetamido-3-(3-fluorophenyl)-propanoate → N-Boc-3-fluoro-L-phenylalanine (114873-01-7,114873-11-9)

Guidance literature:

di-tert-butyl dicarbonate; methyl (S)-2-acetamido-3-(3-fluorophenyl)-propanoate; With dmap; In tetrahydrofuran; at 80 ℃; for 4h; Microwave irradiation; Inert atmosphere;

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/acs.jmedchem.9b01104

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

L-3-fluorophenylalanine

di-tert-butyl dicarbonate

3-fluorophenylboronic acid

Downstream raw materials:

(4S,7S,10S)-10-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-7-(3-fluoro-benzyl)-3,3-dimethyl-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carboxylic acid

N'-methoxy-N'-methyl (S)-N-BOC-(3-fluorophenyl)-alanine amide

(S)-2-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

(S)-2-amino-3-(3-fluorophenyl)propanoic acid hydrochloride

Refernces

• 1、 -. "OPIOID RECEPTOR MODULATORS AND PRODUCTS AND METHODS RELATED THERETO". Page/Page column 110. . Retrieved 2019/10/29.
• 2、 -. "HIV PROTEASE INHIBITORS, COMPOSITIONS CONTAINING THE SAME AND THEIR PHARMACEUTICAL USES". Page/Page column 85. . Retrieved 2010/02/11.