N¹-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N⁴-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine

Base Information

• Chemical Name: N¹-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N⁴-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine
• CAS No.: 174061-55-3
• Molecular Formula: C₃₆H₅₆F₂N₄O₇
• Molecular Weight: 694.86

Synonyms:N¹-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N⁴-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine

Chemical Property of N¹-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N⁴-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine

Chemical Property:

Purity/Quality:

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Technology Process of N¹-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N⁴-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine

There total 7 articles about N¹-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N⁴-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine 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: 68.0%

N1-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-3-hydroxy-N4-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-1,4-pentanediamine → N1-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N4-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine (174061-55-3)

Guidance literature:

With dipyridinium dichromate; 3 A molecular sieve; acetic acid; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1016/0040-4020(95)00896-G

Reference yield:

2-<(benzyloxycarbonyl)amino>-3-cyclohexyl-(2S)-propionaldehyde (105852-47-9) → N1-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N4-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine (174061-55-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / zinc / tetrahydrofuran / reflux; rt, 15 h

2: 97 percent / ammonia gas / diethyl ether / -78 °C

3: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

4: 2.50 g / hydrogen / 10percent palladium on charcoal / ethanol / 12 h / 760 Torr / Ambient temperature

5: 1.) N-methylmorpholine, isobutylchloroformate / 1.) acetonitrile, -20 deg C, 15 min; 2.) acetonitrile, rt, 15 h

6: 68 percent / pyridinium dichromate, 3 Angstroem molecular sieves, glacial acetic acid / CH₂Cl₂ / 15 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; dipyridinium dichromate; dimethylsulfide borane complex; 3 A molecular sieve; ammonia; hydrogen; sodium hydrogencarbonate; sodium carbonate; acetic acid; zinc; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1016/0040-4020(95)00896-G

Reference yield:

N',O-dimethyl-N-benzyloxycarbonyl-L-cyclohexylalanine hydroxamate (118388-23-1) → N1-tert-butoxycarbonyl-5-cyclohexyl-2,2-difluoro-N4-(3-methylbutanoyl-L-O-methyltyrosyl-L-n-valyl)-3-oxo-1,4-pentanediamine (174061-55-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / lithium aluminium hydride / diethyl ether / 1 h / 0 °C

2: 61 percent / zinc / tetrahydrofuran / reflux; rt, 15 h

3: 97 percent / ammonia gas / diethyl ether / -78 °C

4: 1.) BH₃(CH₃)2S; 2.) sat.hydrogen chloride; 3.) NaHCO₃, Na₂CO₃, / 1.) THF, reflux, 4 h; 2.) Et₂O, 0.45 min; 3.) water/THF, rt, 15 h

5: 2.50 g / hydrogen / 10percent palladium on charcoal / ethanol / 12 h / 760 Torr / Ambient temperature

6: 1.) N-methylmorpholine, isobutylchloroformate / 1.) acetonitrile, -20 deg C, 15 min; 2.) acetonitrile, rt, 15 h

7: 68 percent / pyridinium dichromate, 3 Angstroem molecular sieves, glacial acetic acid / CH₂Cl₂ / 15 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; dimethylsulfide borane complex; 3 A molecular sieve; ammonia; hydrogen; sodium hydrogencarbonate; sodium carbonate; acetic acid; zinc; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1016/0040-4020(95)00896-G

upstream raw materials:

2-<(benzyloxycarbonyl)amino>-3-cyclohexyl-(2S)-propionaldehyde

N',O-dimethyl-N-benzyloxycarbonyl-L-cyclohexylalanine hydroxamate

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