(S)-3-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic acid

Base Information

• Chemical Name: (S)-3-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic acid
• CAS No.: 500770-82-1
• Molecular Formula: C15H18 N2 O4
• Molecular Weight: 290.31
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00427430
• Nikkaji Number: J2.066.207G
• Wikidata: Q72447990
• Mol file: 500770-82-1.mol

Synonyms:500770-82-1;(S)-3-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic acid;Boc-(S)-3-Amino-3-(4-cyano-phenyl)-propionic acid;(3S)-3-(4-cyanophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(S)-Boc-4-cyano-beta-Phe-OH;Boc-(S)-3-amino-3-(4-cyanophenyl)propionic acid;SCHEMBL4745227;DTXSID00427430;(S)-3-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoicacid;Boc-D-Phg(4-CN)-(C#CH2)OH;MFCD03427930;AKOS016843982;PS-12449;CS-0154509;(S)-Boc-4-cyano-beta-Phe-OH, >=98.0%;W18476;boc-(s)-3-amino-3-(4-cyanophenyl)propanoic acid;(S)-beta-(tert-Butoxycarbonylamino)-4-cyanohydrocinnamic acid;(3S)-3-[(tert-Butoxycarbonyl)amino]-3-(4-cyanophenyl)propanoic acid

Chemical Property of (S)-3-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic acid

Chemical Property:

• Melting Point: 127℃
• Boiling Point: 491.5±45.0 °C(Predicted)
• PKA: 4.17±0.10(Predicted)
• PSA: 99.42000
• Density: 1.22
• LogP: 2.98968
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 290.12665706
• Heavy Atom Count: 21
• Complexity: 425

Purity/Quality:

99% ^*data from raw suppliers

Boc-(S)-3-amino-3-(4-cyanophenyl)propionicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-3-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic acid

There total 3 articles about (S)-3-((tert-Butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic 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:

di-tert-butyl dicarbonate (24424-99-5) + ethyl (S)-3-butanoylamino-3-(4-cyanophenyl)propanoate (738606-23-0) → (S)-3-(tert-butoxycarbonylamino)-3-(4-cyanophenyl)propanoic acid (500770-82-1,501015-22-1,282524-88-3)

Guidance literature:

ethyl (S)-3-butanoylamino-3-(4-cyanophenyl)propanoate; With hydrogenchloride; for 3h; Heating;

di-tert-butyl dicarbonate; With potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 5h;

DOI:10.1016/j.tetasy.2004.05.012

Reference yield:

(+/-)-3-amino-3-(4-cyanophenyl)propanoic acid (80971-95-5) → (S)-3-(tert-butoxycarbonylamino)-3-(4-cyanophenyl)propanoic acid (500770-82-1,501015-22-1,282524-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1.33 g / SOCl₂

2.1: Candida antarctica lipase A / diethyl ether / 1 h / 20 °C

3.1: hydrochloric acid / 3 h / Heating

3.2: K₂CO₃ / dioxane; H₂O / 5 h / 20 °C

With hydrogenchloride; thionyl chloride; Candida antarctica Lipase A; In diethyl ether;

DOI:10.1016/j.tetasy.2004.05.012

Reference yield:

ethyl (+/-)-3-amino-3-(4-cyanophenyl)propanoate (288848-50-0) → (S)-3-(tert-butoxycarbonylamino)-3-(4-cyanophenyl)propanoic acid (500770-82-1,501015-22-1,282524-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Candida antarctica lipase A / diethyl ether / 1 h / 20 °C

2.1: hydrochloric acid / 3 h / Heating

2.2: K₂CO₃ / dioxane; H₂O / 5 h / 20 °C

With hydrogenchloride; Candida antarctica Lipase A; In diethyl ether;

DOI:10.1016/j.tetasy.2004.05.012

upstream raw materials:

di-tert-butyl dicarbonate

ethyl (S)-3-butanoylamino-3-(4-cyanophenyl)propanoate

(+/-)-3-amino-3-(4-cyanophenyl)propanoic acid

ethyl (+/-)-3-amino-3-(4-cyanophenyl)propanoate

Downstream raw materials:

tert-butyl {(1S)-1-(4-cyanophenyl)-3-[methoxy(methyl)amino]-3-oxopropyl}carbamate

C₁₂H₁₅N₃O₂

4-{(2S)-4-methyl-6-oxo-5-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridin-2-yl}benzonitrile

N-[(1S)-1-(4-cyanophenyl)-3-oxobutyl]-2-[3-(trifluoromethyl)phenyl]acetamide