(2S)-tert-Butoxycarbonylaminophenylacetonitrile

Base Information

• Chemical Name: (2S)-tert-Butoxycarbonylaminophenylacetonitrile
• CAS No.: 177723-19-2
• Molecular Formula: C13H16N2O2
• Molecular Weight: 232.282
• DSSTox Substance ID: DTXSID90365195
• Nikkaji Number: J1.206.737B
• Wikidata: Q82149661
• Mol file: 177723-19-2.mol

Synonyms:177723-19-2;ZINC02154129;(2S)-tert-Butoxycarbonylaminophenylacetonitrile;SCHEMBL5740500;DTXSID90365195

Chemical Property of (2S)-tert-Butoxycarbonylaminophenylacetonitrile

Chemical Property:

• Melting Point: 120.5-121.3 °C
• Boiling Point: 367.8±35.0 °C(Predicted)
• PSA: 65.61000
• Density: 1.099±0.06 g/cm3(Predicted)
• LogP: 2.98038
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 232.121177757
• Heavy Atom Count: 17
• Complexity: 305

Purity/Quality:

tert-butylcyano(phenyl)methylcarbamate >95% ^*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(C#N)C1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C#N)C1=CC=CC=C1

Technology Process of (2S)-tert-Butoxycarbonylaminophenylacetonitrile

There total 10 articles about (2S)-tert-Butoxycarbonylaminophenylacetonitrile 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) + C32H29N4OP (1236163-01-1) → (S)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile (177723-19-2) + N1,N2-bis(naphthalen-1-ylmethyl)ethane-1,2-diamine

Guidance literature:

C₃₂H₂₉N₄OP; With hydrogenchloride; methanol; In water; at 20 ℃; for 2h;

di-tert-butyl dicarbonate; With triethylamine; In dichloromethane; water; at 20 ℃;

DOI:10.1039/c0cc00287a

Reference yield: 99.0%

trimethylsilyl cyanide (7677-24-9) + benzaldehyde N-boc imine (150884-50-7) → (S)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile (177723-19-2)

Guidance literature:

With tetrabutoxytitanium; water; N-(2'-hydroxyphenyl)methyl-(S)-2-amino-3,3-dimethyl-butan-1-ol; In toluene; butan-1-ol; at 20 ℃; for 0.25h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol902540h

Reference yield: 90.0%

Boc-L-Phg-NH2 (143978-92-1) → (S)-2-N-tert-butoxycarbonylamino-2-phenylethanenitrile (177723-19-2)

Guidance literature:

With 4-methyl-morpholine; iodine; triphenylphosphine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1007/s10989-020-10101-y

upstream raw materials:

hydrogen cyanide

tert-butyl benzylidenecarbamate

di-tert-butyl dicarbonate

(S)-α-phenylglycinenitrile

Downstream raw materials:

(S)-2-phenylglycine

(S)-N₁-tert-butoxycarbonyl-1-phenyl-1,2-ethanediamine

C₁₃H₁₇N₅O₂