N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester

Base Information

• Chemical Name: N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester
• CAS No.: 286958-56-3
• Molecular Formula: C₁₈H₂₁NO₇S₂
• Molecular Weight: 427.499

Synonyms:N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester

Chemical Property of N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester

There total 4 articles about N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl 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: 95.0%

ethyl bromoacetate (105-36-2) + 3-(1,3-dioxolan-2-yl)-N-(3-methoxyphenyl)-2-thiophenesulfonamide (286958-43-8) → N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester (286958-56-3)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; tert-butyl alcohol; at 0 - 5 ℃;

DOI:10.1016/S0968-0896(00)00026-2

Reference yield:

3-(1,3-dioxolan-2-yl)-N-(3-methoxyphenyl)-2-thiophenesulfonamide (286958-43-8) → N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester (286958-56-3)

Guidance literature:

In N,N-dimethyl-formamide;

Reference yield:

2-(thiophen-3-yl)-1,3-dioxolane (13250-82-3) → N-[[3-(1,3-dioxolan-2-yl)thien-2-yl]sulfonyl]-N-(3-methoxyphenyl)-glycine ethyl ester (286958-56-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.83 h / -70 °C

1.2: SO₂ / tetrahydrofuran; hexane / 1 h / 20 °C

1.3: N-chlorosuccinimide / CH₂Cl₂ / 18 h

2.1: 62 percent / Et₃N / CH₂Cl₂ / 20 °C

3.1: 95 percent / potassium t-butoxide / 2-methyl-propan-2-ol; dimethylformamide / 0 - 5 °C

With n-butyllithium; potassium tert-butylate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Metallation / 1.2: Substitution / 1.3: Chlorination / 2.1: Substitution / 3.1: Substitution;

DOI:10.1016/S0968-0896(00)00026-2

upstream raw materials:

ethyl bromoacetate

3-(1,3-dioxolan-2-yl)-N-(3-methoxyphenyl)-2-thiophenesulfonamide

2-(thiophen-3-yl)-1,3-dioxolane

3-(1,3-dioxolan-2-yl)thiophene-2-sulfonyl chloride

Downstream raw materials:

2-(3-methoxy-phenyl)-3-morpholin-4-ylmethyl-1,1-dioxo-1,2-dihydro-1λ⁶-thieno[3,2-e][1,2]thiazine-6-sulfonic acid amide

3-[(2-hydroxy-ethylamino)-methyl]-2-(3-methoxy-phenyl)-1,1-dioxo-1,2-dihydro-1λ⁶-thieno[3,2-e][1,2]thiazine-6-sulfonic acid amide

3-Hydroxymethyl-2-(3-methoxyphenyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

Ethyl 2-(3-methoxyphenyl)-2H-thieno[3,2-e]-1,2-thiazine-3-carboxylate 1,1-dioxide

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