4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester

Base Information

• Chemical Name: 4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester
• CAS No.: 198905-08-7
• Molecular Formula: C₂₇H₂₇N₃O₄
• Molecular Weight: 457.529
• Mol file: 198905-08-7.mol

Synonyms:4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester

Chemical Property of 4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester

There total 1 articles about 4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester 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: 39.0%

Boc-L-phenylalaninal (72155-45-4) + potassium cyanide (151-50-8) → 4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester (198905-08-7) + C27H27N3O4

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; water; at 0 ℃;

DOI:10.1016/S0040-4039(98)00897-1

Reference yield: 53.0%

t-butoxycarbonylhydrazine (870-46-2) + 4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester (198905-08-7) → 4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-(tert-butoxycarbonyl-hydrazonomethyl)-3-phenyl-propyl ester (198905-09-8)

Guidance literature:

With hydrogen; acetic acid; nickel; In methanol; under 750.06 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(98)00897-1

Reference yield:

4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-cyano-3-phenyl-propyl ester (198905-08-7) → 1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane (198904-86-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 53 percent / H₂, AcOH / Raney Ni / methanol / 750.06 Torr / Ambient temperature

2: NaBH₃CN, TsOH / 1,2-dimethoxy-ethane / Ambient temperature

3: 1.) aq. borax; 2.) MTBD

4: 60 percent / DIBAH / 2.5 h / 0 °C

With borax; hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; nickel; In methanol; 1,2-dimethoxyethane;

DOI:10.1016/S0040-4039(98)00897-1

upstream raw materials:

Boc-L-phenylalaninal

potassium cyanide

Downstream raw materials:

4-Pyridin-2-yl-benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-1-(tert-butoxycarbonyl-hydrazonomethyl)-3-phenyl-propyl ester

1-(4-(pyridin-2-yl)-phenyl)-1-oxo-5(S)-2,5-di[(tert-butoxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane

1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane