(R)-((Allyloxy)carbonylamino)(4-hydroxyphenyl)acetic acid

Base Information

• Chemical Name: (R)-((Allyloxy)carbonylamino)(4-hydroxyphenyl)acetic acid
• CAS No.: 84792-41-6
• Molecular Formula: C12H13 N O5
• Molecular Weight: 251.239
• Hs Code.: 2924299090
• European Community (EC) Number: 284-161-4
• DSSTox Substance ID: DTXSID60233832
• Nikkaji Number: J309.445F
• Wikidata: Q83115495
• Mol file: 84792-41-6.mol

Synonyms:84792-41-6;EINECS 284-161-4;(R)-((Allyloxy)carbonylamino)(4-hydroxyphenyl)acetic acid;DTXSID60233832;NS00038654;EN300-25952982;(2R)-2-(4-hydroxyphenyl)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}acetic acid

Chemical Property of (R)-((Allyloxy)carbonylamino)(4-hydroxyphenyl)acetic acid

Chemical Property:

• Vapor Pressure: 1.1E-09mmHg at 25°C
• Boiling Point: 471.2°C at 760 mmHg
• Flash Point: 238.8°C
• PSA: 99.35000
• Density: 1.325g/cm³
• LogP: 1.63450
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 251.07937252
• Heavy Atom Count: 18
• Complexity: 310

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC(=O)NC(C1=CC=C(C=C1)O)C(=O)O
• Isomeric SMILES: C=CCOC(=O)N[C@H](C1=CC=C(C=C1)O)C(=O)O

Technology Process of (R)-((Allyloxy)carbonylamino)(4-hydroxyphenyl)acetic acid

There total 2 articles about (R)-((Allyloxy)carbonylamino)(4-hydroxyphenyl)acetic acid 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: 98.0%

D-4-hydroxyphenylglycine (22818-40-2) + N-(allyloxycarbonyloxy)succinimide (135544-68-2) → (R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine (84792-41-6)

Guidance literature:

With sodium hydrogencarbonate; In acetone; at 20 ℃; for 5h;

DOI:10.1039/b418908f

Reference yield: 50.0%

D-4-hydroxyphenylglycine (22818-40-2) + Allyl chloroformate (2937-50-0) → (R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine (84792-41-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; diethyl ether; water; for 1h; ice bath;

DOI:10.1021/jm00401a020

Reference yield:

(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycine (84792-41-6) → allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-vinyl-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: EEDQ / ethyl acetate / 3 h / Ambient temperature

2: 81 percent / pyridine, 30percent H₂O₂ / CH₂Cl₂; H₂O / 0.33 h

With pyridine; dihydrogen peroxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; water; ethyl acetate;

DOI:10.1021/jm00401a020

upstream raw materials:

D-4-hydroxyphenylglycine

Allyl chloroformate

N-(allyloxycarbonyloxy)succinimide

Downstream raw materials:

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

(6S,7S)-7-[(R)-2-Allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-methyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-(chloromethyl)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

(6S,7S)-7-[(R)-2-Allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-8-oxo-3-propyl-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester