rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate

Base Information

• Chemical Name: rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate
• CAS No.: 501085-40-1
• Molecular Formula: C₁₄H₂₁NO₅
• Molecular Weight: 283.324

Synonyms:rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate

Chemical Property of rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate

There total 4 articles about rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate 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:

(1R,2S,3S,4S)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (501085-41-2) → ethyl-3-hydroxybenzoate (7781-98-8) + rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate (501085-40-1)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -50 - 25 ℃;

DOI:10.1021/ol0269704

Reference yield:

(E)-ethyl 3-nitroacrylate (5941-50-4,1851-82-7,105576-14-5) → rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate (501085-40-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CHCl₃ / 120 h / -20 °C

2.1: zinc; HCl / ethanol

2.2: diisopropylethylamine

3.1: potassium hexamethyldisilazide / tetrahydrofuran / -50 - 25 °C

With hydrogenchloride; potassium hexamethylsilazane; zinc; In tetrahydrofuran; ethanol; chloroform; 1.1: Diels-Alder reaction;

DOI:10.1021/ol0269704

Reference yield:

ethyl (1SR,2RS,3RS,4RS)-3-nitro-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate (84751-41-7,89299-58-1,89299-59-2) → rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate (501085-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc; HCl / ethanol

1.2: diisopropylethylamine

2.1: potassium hexamethyldisilazide / tetrahydrofuran / -50 - 25 °C

With hydrogenchloride; potassium hexamethylsilazane; zinc; In tetrahydrofuran; ethanol;

DOI:10.1021/ol0269704

upstream raw materials:

(1R,2S,3S,4S)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

(E)-ethyl 3-nitroacrylate

ethyl (1SR,2RS,3RS,4RS)-3-nitro-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

ethyl acrylate

Downstream raw materials:

tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

(5S,6S)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid

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