7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid

Base Information

• Chemical Name: 7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid
• CAS No.: 722492-51-5
• Molecular Formula: C₃₁H₅₂N₄O₉
• Molecular Weight: 624.775

Synonyms:7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid

Chemical Property of 7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid

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Technology Process of 7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid

There total 10 articles about 7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic 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:

7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-hydroxy-heptanoic acid → 7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid (722492-51-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃;

DOI:10.1021/jm011110z

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid (722492-51-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 15.8 g / Et₃N / dimethylformamide / 20 °C / pH 8

2.1: H₂; aq. HCl / 10percent Pd/C / dimethylformamide / 2 h / 20 °C

3.1: HOBt / dimethylformamide / 0 °C

3.2: Et₃N / dimethylformamide / 0 - 20 °C / pH 8

4.1: aq. NaOH / dioxane / 20 °C / pH 10 - 10.5

5.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium hydroxide; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; triethylamine; 10percent Pd/C; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011110z

Reference yield:

Z-Lys(Boc)-OH (2389-60-8) → 7-tert-butoxycarbonylamino-3-{[1-(2-tert-butoxycarbonylamino-3-cyclohexyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-2-oxo-heptanoic acid (722492-51-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / TBTU; Et₃N / CH₂Cl₂ / 2 h / 20 °C / pH 8

2.1: DiBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: 26.3 g / aq. triethylbenzylammonium chloride / CH₂Cl₂

4.1: HCl / diethyl ether / -20 - 4 °C

4.2: water / diethyl ether / 16 h / 5 - 20 °C

5.1: 15.8 g / Et₃N / dimethylformamide / 20 °C / pH 8

6.1: H₂; aq. HCl / 10percent Pd/C / dimethylformamide / 2 h / 20 °C

7.1: HOBt / dimethylformamide / 0 °C

7.2: Et₃N / dimethylformamide / 0 - 20 °C / pH 8

8.1: aq. NaOH / dioxane / 20 °C / pH 10 - 10.5

9.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With hydrogenchloride; sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; diisobutylaluminium hydride; benzotriazol-1-ol; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; 10percent Pd/C; In 1,4-dioxane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011110z

upstream raw materials:

di-tert-butyl dicarbonate

Z-Lys(Boc)-OH

N^α-(benzyloxycarbonyl)-N^ε-(tert-butoxycarbonyl)-L-lysine methyl ester

tert-butyl-N-[(5S)-5-(benzyloxycarbonylamino)-6-oxo-hexyl]carbamate

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