N¹-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N⁴-dimethylcarbamoylmethyl-N⁴-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide

Base Information

• Chemical Name: N¹-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N⁴-dimethylcarbamoylmethyl-N⁴-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide
• CAS No.: 160447-15-4
• Molecular Formula: C₅₃H₆₇N₅O₅
• Molecular Weight: 854.145

Synonyms:N¹-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N⁴-dimethylcarbamoylmethyl-N⁴-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide

Chemical Property of N¹-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N⁴-dimethylcarbamoylmethyl-N⁴-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide

Chemical Property:

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Technology Process of N¹-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N⁴-dimethylcarbamoylmethyl-N⁴-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide

There total 6 articles about N¹-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N⁴-dimethylcarbamoylmethyl-N⁴-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide 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: 65.0%

N,N-dimethyl-2-<<1(S)-phenylethyl>amino>acetamide (160937-99-5) + (R)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-(1-trityl-1H-imidazol-4-ylmethyl)-succinamic acid (160447-21-2) → N1-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N4-dimethylcarbamoylmethyl-N4-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide (160447-15-4)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 5h;

DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride (104882-45-3) → N1-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N4-dimethylcarbamoylmethyl-N4-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide (160447-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 °C

2: 99 percent / H₂ / Pd/C / ethanol / 2.5 h / 760 Torr

3: 65 percent / BOP*PF₆, i-Pr₂NEt / dimethylformamide / 5 h / 25 °C

With hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

4(S)-(1-methylethyl)-3-[1-oxo-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propyl]-2-oxazolidinone (160447-11-0) → N1-(1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-N4-dimethylcarbamoylmethyl-N4-(1-phenyl-ethyl)-2-(1-trityl-1H-imidazol-4-ylmethyl)-succinamide (160447-15-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 64 percent / NaHMDS / tetrahydrofuran / -78 °C / 1.) 45 min, 2.) 2 h

2: 30 percent H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

3: i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 °C

4: 99 percent / H₂ / Pd/C / ethanol / 2.5 h / 760 Torr

5: 65 percent / BOP*PF₆, i-Pr₂NEt / dimethylformamide / 5 h / 25 °C

With lithium hydroxide; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(98)00265-X

upstream raw materials:

N,N-dimethyl-2-<<1(S)-phenylethyl>amino>acetamide

(R)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-(1-trityl-1H-imidazol-4-ylmethyl)-succinamic acid

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride

4(S)-(1-methylethyl)-3-[1-oxo-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propyl]-2-oxazolidinone

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