4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid

Base Information

• Chemical Name: 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid
• CAS No.: 204141-32-2
• Molecular Formula: C₁₄H₁₉NO₅S₂
• Molecular Weight: 345.441

Synonyms:4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid

Chemical Property of 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid

Chemical Property:

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Technology Process of 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid

There total 4 articles about 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid 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:

D-penicillamine methyl ester hydrochloride (34297-27-3) → 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid (204141-32-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 20 °C

2: Et₃N / dioxane; H₂O / 18 h / 20 °C

3: Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

4: LiI; pyridine / 3 h / Heating

With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; 1: Alkylation / 2: sulfonylation / 3: Cyclization / 4: demethylation;

DOI:10.1021/jm990330y

Reference yield:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid (204141-32-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / dioxane; H₂O / 18 h / 20 °C

2: Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

3: LiI; pyridine / 3 h / Heating

With pyridine; triethylamine; triphenylphosphine; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; water; 1: sulfonylation / 2: Cyclization / 3: demethylation;

DOI:10.1021/jm990330y

Reference yield:

(S)-2-Amino-3-(2-hydroxy-ethylsulfanyl)-3-methyl-butyric acid methyl ester → 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-3(S)-thiomorpholinecarboxylic acid (204141-32-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / dioxane; H₂O / 18 h / 20 °C

2: Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

3: LiI; pyridine / 3 h / Heating

With pyridine; triethylamine; triphenylphosphine; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; water; 1: sulfonylation / 2: Cyclization / 3: demethylation;

DOI:10.1021/jm990330y

upstream raw materials:

D-penicillamine methyl ester hydrochloride

4-methoxy-phenyl-sulphonyl chloride

methyl N-[(4-methoxyphenyl)sulfonyl]-S-(2-hydroxyethyl)-D-penicillamine

Downstream raw materials:

(S)-4-(4-Methoxy-benzenesulfonyl)-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxyamide

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