(4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

Base Information

• Chemical Name: (4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate
• CAS No.: 1613309-48-0
• Molecular Formula: C₃₇H₃₃N₂O₄P
• Molecular Weight: 600.654

Synonyms:(4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

Chemical Property of (4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

Chemical Property:

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Technology Process of (4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

There total 5 articles about (4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-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:

P,P-diphenyl-N-[1-(4-methoxyphenyl)ethylidene]phosphinic amide (866540-37-6) + diphenylmethyl 2-isocyanoacetate (123176-34-1) → (4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate (1613309-48-0) + diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

Guidance literature:

P,P-diphenyl-N-[1-(4-methoxyphenyl)ethylidene]phosphinic amide; With N-[(4β,8α,9S)-10,11-dihydrocinchonan-9-yl]-2-(diphenylphosphino)benzamide; silver(l) oxide; In ethyl acetate; at -20 ℃; for 0.0833333h; Molecular sieve;

diphenylmethyl 2-isocyanoacetate; In ethyl acetate; at -20 ℃; for 60h; Overall yield = 96 %; Overall yield = 92 mg; stereoselective reaction; Molecular sieve;

DOI:10.1002/anie.201309719

Reference yield:

4-methoxyacetophenone oxime (2475-92-5) → (4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate (1613309-48-0) + diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane; hexane / 0.17 h / -45 °C

1.2: 16.33 h / -45 - 20 °C

2.1: N-[(4β,8α,9S)-10,11-dihydrocinchonan-9-yl]-2-(diphenylphosphino)benzamide; silver(l) oxide / ethyl acetate / 0.08 h / -20 °C / Molecular sieve

2.2: 60 h / -20 °C / Molecular sieve

With N-[(4β,8α,9S)-10,11-dihydrocinchonan-9-yl]-2-(diphenylphosphino)benzamide; triethylamine; silver(l) oxide; In hexane; dichloromethane; ethyl acetate;

DOI:10.1002/anie.201309719

Reference yield:

1-(4-methoxyphenyl)ethanone (100-06-1) → (4R,5S)-diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate (1613309-48-0) + diphenylmethyl 1-(diphenylphosphoryl)-5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 20 h / 20 °C / Reflux

2.1: triethylamine / dichloromethane; hexane / 0.17 h / -45 °C

2.2: 16.33 h / -45 - 20 °C

3.1: N-[(4β,8α,9S)-10,11-dihydrocinchonan-9-yl]-2-(diphenylphosphino)benzamide; silver(l) oxide / ethyl acetate / 0.08 h / -20 °C / Molecular sieve

3.2: 60 h / -20 °C / Molecular sieve

With N-[(4β,8α,9S)-10,11-dihydrocinchonan-9-yl]-2-(diphenylphosphino)benzamide; hydroxylamine hydrochloride; sodium acetate; triethylamine; silver(l) oxide; In ethanol; hexane; dichloromethane; water; ethyl acetate;

DOI:10.1002/anie.201309719

upstream raw materials:

4-methoxyacetophenone oxime

1-(4-methoxyphenyl)ethanone

1,1-Diphenylmethanol

diphenylmethyl 2-formamidoacetate

Downstream raw materials:

(4R,5S)-diphenylmethyl 5-(4-methoxyphenyl)-5-methyl-4,5-dihydro-1H-imidazole-4-carboxylate

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