methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate

Base Information

• Chemical Name: methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate
• CAS No.: 180322-80-9
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347

Synonyms:methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate

Chemical Property of methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate

There total 5 articles about methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate 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:

(1S,2S)-(E)-1-carboxy-1-(methoxycarbonyl)-2-phenylcyclopropane (180322-77-4) → methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate (180322-80-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / K₂CO₃

2: 75 percent / aq. NaOH / methanol / 2 h

3: Et₃N, diphenylphosphoryl azide / 2-methyl-propan-2-ol; hexane / Heating

4: 2-methyl-propan-2-ol; hexane / Heating

With sodium hydroxide; diphenylphosphoranyl azide; potassium carbonate; triethylamine; In methanol; hexane; tert-butyl alcohol;

DOI:10.1021/ja9604931

Reference yield:

dimethyl (2S)-2-phenylcyclopropane-1,1-dicarboxylate (158800-60-3) → methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate (180322-80-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / aq. NaOH / methanol / 2 h

2: Et₃N, diphenylphosphoryl azide / 2-methyl-propan-2-ol; hexane / Heating

3: 2-methyl-propan-2-ol; hexane / Heating

With sodium hydroxide; diphenylphosphoranyl azide; triethylamine; In methanol; hexane; tert-butyl alcohol;

DOI:10.1021/ja9604931

Reference yield:

(1S,2S)-2-phenyl-1-(pyrrolidin-1-ylcarbonyl)cyclopropanecarboxylic acid (158800-59-0) → methyl (1R,2S)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylate (180322-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, diphenylphosphoryl azide / 2-methyl-propan-2-ol; hexane / Heating

2: 2-methyl-propan-2-ol; hexane / Heating

With diphenylphosphoranyl azide; triethylamine; In hexane; tert-butyl alcohol;

DOI:10.1021/ja9604931

upstream raw materials:

di-tert-butyl dicarbonate

methyl (1R,2S)-1-amino-2-phenylcyclopropanecarboxylate

(1S,2S)-(E)-1-carboxy-1-(methoxycarbonyl)-2-phenylcyclopropane

dimethyl (2S)-2-phenylcyclopropane-1,1-dicarboxylate

Downstream raw materials:

(1R,2S)-1-tert-Butoxycarbonylamino-2-phenyl-cyclopropanecarboxylic acid

(+)-(2R)-Cyclopropyl-E-phenylalanine

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