tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate

Base Information

• Chemical Name: tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate
• CAS No.: 174488-20-1
• Molecular Formula: C₁₇H₂₃N₅O₄
• Molecular Weight: 361.401
• Mol file: 174488-20-1.mol

Synonyms:tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate

Chemical Property of tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate

There total 6 articles about tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate 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: 84.0%

citric acid (77-92-9,906507-37-7) + tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-cyanobutyrate (174488-19-8) → tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate (174488-20-1)

Guidance literature:

With ammonium chloride; In hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield: 84.0%

tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-cyanobutyrate (174488-19-8) → tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate (174488-20-1)

Guidance literature:

With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 90 - 95 ℃; for 20h;

DOI:10.1021/jm991119p

Reference yield:

N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester (51644-83-8) → tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(5-tetrazolyl)butyrate (174488-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / tetrahydrofuran / 0.17 h / -15 °C

2: NH₃ / tetrahydrofuran / 0.5 h / -5 - 5 °C

3: 86 percent / POCl₃; pyridine / CH₂Cl₂ / 15 h / 20 °C

4: 84 percent / NaN₃; NH₄Cl / dimethylformamide / 20 h / 90 - 95 °C

With pyridine; sodium azide; ammonia; ammonium chloride; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm991119p

upstream raw materials:

tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-cyanobutyrate

N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester

tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-carbamoylbutyrate

citric acid

Downstream raw materials:

tert-butyl (4R)-4-{N-[N-(benzyloxycarbonyl)-α-tert-butyl-L-γ-glutamyl]amino}-4-(5-tetrazolyl)butyrate

tert-butyl (4R)-4-{N-{N-{4-[N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-N-(prop-2-ynyl)amino]benzoyl}-α-tert-butyl-L-γ-glutamyl}amino}-4-(5-tetrazolyl)butyrate