N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester

Base Information

• Chemical Name: N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester
• CAS No.: 910116-97-1
• Molecular Formula: C₃₀H₃₈N₂O₆
• Molecular Weight: 522.642
• Mol file: 910116-97-1.mol

Synonyms:N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester

Chemical Property of N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester

There total 1 articles about N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl 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: 43.0%

(1R,2R)-1,2-diaminocyclohexane (20439-47-8) + 3-(benzyloxy)-2,2-dimethyl-3-oxopropanoic acid (86507-74-6) → N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester (910116-97-1)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/jo060767v

Reference yield:

N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester (910116-97-1) → 2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-N-{(1R,2R)-2-[2-((S)-4-isopropyl-4,5-dihydro-oxazol-2-yl)-2-methyl-propionylamino]-cyclohexyl}-isobutyramide

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / H₂ / Pd/C / ethanol / 24 h / 20 °C

2: 62 percent / HBTU; Et₃N / acetonitrile / 2 h

3: 22 percent / bis(2-methoxyethyl)aminosulfur trifluoride / tetrahydrofuran; CH₂Cl₂ / 5 h / -10 - 20 °C

With hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jo060767v

Reference yield:

N-[(1R,2R)-2-(2-Benzyloxycarbonyl-2-methyl-propionylamino)-cyclohexyl]-2,2-dimethyl-malonamic acid benzyl ester (910116-97-1) → N-((S)-1-Hydroxymethyl-2-methyl-propyl)-N'-{(1R,2R)-2-[2-((S)-1-hydroxymethyl-2-methyl-propylcarbamoyl)-2-methyl-propionylamino]-cyclohexyl}-2,2-dimethyl-malonamide (910116-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / H₂ / Pd/C / ethanol / 24 h / 20 °C

2: 62 percent / HBTU; Et₃N / acetonitrile / 2 h

With hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; palladium on activated charcoal; In ethanol; acetonitrile;

DOI:10.1021/jo060767v

upstream raw materials:

(1R,2R)-1,2-diaminocyclohexane

3-(benzyloxy)-2,2-dimethyl-3-oxopropanoic acid

Downstream raw materials:

N-((S)-1-Hydroxymethyl-2-methyl-propyl)-N'-{(1R,2R)-2-[2-((S)-1-hydroxymethyl-2-methyl-propylcarbamoyl)-2-methyl-propionylamino]-cyclohexyl}-2,2-dimethyl-malonamide