1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea

Base Information

• Chemical Name: 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea
• CAS No.: 216692-41-0
• Molecular Formula: C₃₆H₄₇N₃O₆SSi
• Molecular Weight: 677.937

Synonyms:1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea

Chemical Property of 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea

There total 8 articles about 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea (216692-41-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

2: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

3: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

4: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

5: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

6: Et₃N / dioxane / 10 h / 100 °C

With 1H-imidazole; dmap; lithium borohydride; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine (118329-82-1) → 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea (216692-41-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

2: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

3: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

4: Et₃N / dioxane / 10 h / 100 °C

With 1H-imidazole; dmap; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00821-7

Reference yield:

N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester (16257-73-1) → 1-[(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-3-{2-[1-ethoxy-meth-(E)-ylidene]-butyryl}-urea (216692-41-0)

Guidance literature:

Multi-step reaction with 5 steps

1: LiBH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 1 h

2: 100 percent / imidazole, DMAP / CH₂Cl₂ / 18 h

3: 87 percent / aq. NaN₃ / dimethylformamide / 1.) 70 deg C, 5 h, 2.) room temperature, 18 h

4: 100 percent / H₂ / Pd/C / ethanol; H₂O; ethyl acetate / 2.5 h

5: Et₃N / dioxane / 10 h / 100 °C

With 1H-imidazole; dmap; lithium borohydride; sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00821-7

upstream raw materials:

N-ethoxycarbonyl-(E)-2-ethoxymethylene-butyramide

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine

(2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

Acetic acid (2S,4S)-4-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione

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