methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxybenzoate

Base Information

• Chemical Name: methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxybenzoate
• CAS No.: 1346123-14-5
• Molecular Formula: C₂₀H₂₃NO₆S
• Molecular Weight: 405.472

Synonyms:methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxybenzoate

Chemical Property of methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxybenzoate

Chemical Property:

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Technology Process of methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxybenzoate

There total 2 articles about methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxybenzoate 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:

(+)-3-benzyloxymethyl-1,2-thiazolidine 1,1-dioxide + methyl 4-bromo-2-methoxybenzoate (139102-34-4) → methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methoxybenzoate (1346123-14-5)

Guidance literature:

With copper(l) iodide; potassium carbonate; potassium iodide; N,N`-dimethylethylenediamine; In toluene; for 8h; Reflux;

Reference yield:

(2S)-2-amino-3-(benzyloxy)propan-1-ol (58577-88-1) → methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methoxybenzoate (1346123-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / 20 °C / Cooling with ice

1.2: 5 h / 80 °C

1.3: -70 - 20 °C

2.1: potassium iodide; potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine / toluene / 8 h / Reflux

With copper(l) iodide; potassium carbonate; triethylamine; potassium iodide; N,N`-dimethylethylenediamine; In tetrahydrofuran; toluene;

Reference yield:

methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methoxybenzoate (1346123-14-5) + 1-(2,4-dimethylphenyl)piperazine (1013-76-9) → (S)-[4-(3-benzyloxymethyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-methoxyphenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone (1346124-56-8)

Guidance literature:

methyl (S)-4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxybenzoate; With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 4h;

1-(2,4-dimethylphenyl)piperazine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20 ℃;

upstream raw materials:

methyl 4-bromo-2-methoxybenzoate

(2S)-2-amino-3-(benzyloxy)propan-1-ol

Downstream raw materials:

(S)-[4-(3-benzyloxymethyl-1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-2-methoxyphenyl][4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

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