3-{4-[(tert-Butoxycarbonyl)amino]phenyl}prop-2-enoic acid

Base Information

• Chemical Name: 3-{4-[(tert-Butoxycarbonyl)amino]phenyl}prop-2-enoic acid
• CAS No.: 131818-18-3
• Molecular Formula: C14H17NO4
• Molecular Weight: 263.293
• DSSTox Substance ID: DTXSID00707688
• Mol file: 131818-18-3.mol

Synonyms:131818-18-3;3-{4-[(tert-Butoxycarbonyl)amino]phenyl}prop-2-enoic acid;DTXSID00707688;IJZRVXKMOGZXQD-UHFFFAOYSA-N;3-(4-tert-butoxycarbonylamino-phenyl)-acrylic acid

Chemical Property of 3-{4-[(tert-Butoxycarbonyl)amino]phenyl}prop-2-enoic acid

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 349

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=CC=C(C=C1)C=CC(=O)O

Technology Process of 3-{4-[(tert-Butoxycarbonyl)amino]phenyl}prop-2-enoic acid

There total 5 articles about 3-{4-[(tert-Butoxycarbonyl)amino]phenyl}prop-2-enoic 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: 42.0%

3-(4-((tert-butoxycarbonyl)amino)phenyl)propanoic acid (149506-05-8) → p-(N-tert-butoxycarbonyl)aminocinnamic acid (131818-18-3)

Guidance literature:

With 6-(quinolin-2-yl)pyridin-2(1H)-one; sodium acetate; palladium diacetate; lithium carbonate; silver carbonate; In 1,4-dioxane; tert-Amyl alcohol; at 100 ℃; for 16h; Inert atmosphere;

DOI:10.1126/science.abl3939

Reference yield:

malonic acid (141-82-2) + 4-((tert-butoxycarbonyl)amino)benzaldehyde (144072-30-0) → p-(N-tert-butoxycarbonyl)aminocinnamic acid (131818-18-3)

Guidance literature:

With morpholine; In toluene; at 110 ℃; for 3h; Dean-Stark;

DOI:10.1021/acs.oprd.0c00216

Reference yield:

4-nitrophenylacrylic acid tert-butyl ester (209344-13-8) → p-(N-tert-butoxycarbonyl)aminocinnamic acid (131818-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tin(ll) chloride / ethanol / 0.5 h / 70 °C

2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 4 °C

3: sodium hydrogencarbonate / 1,4-dioxane; water / 20 °C

With sodium hydrogencarbonate; trifluoroacetic acid; tin(ll) chloride; In 1,4-dioxane; ethanol; dichloromethane; water;

upstream raw materials:

4-nitrophenylacrylic acid tert-butyl ester

4-nitrobenzaldehdye

4-aminocinnamic acid tert-butyl ester

malonic acid

Downstream raw materials:

8-O-(4-aminocinnamoyl)-8-O-debutanoylthapsigargin