methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine

Base Information

• Chemical Name: methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine
• CAS No.: 253194-75-1
• Molecular Formula: C₁₆H₂₅NO₆S₂
• Molecular Weight: 391.51

Synonyms:methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine

Chemical Property of methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine

Chemical Property:

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Technology Process of methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine

There total 2 articles about methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine 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:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + (S)-2-Amino-3-(3-hydroxy-propylsulfanyl)-3-methyl-butyric acid methyl ester → methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine (253194-75-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1021/jm990330y

Reference yield:

D-penicillamine methyl ester hydrochloride (34297-27-3) → methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine (253194-75-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: Et₃N / dioxane; H₂O / 18 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide; 1: Alkylation / 2: sulfonylation;

DOI:10.1021/jm990330y

Reference yield: 87.0%

methyl N-[(4-methoxyphenyl)sulfonyl]-S-(3-hydroxypropyl)-D-penicillamine (253194-75-1) → methyl 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate (204129-67-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm990330y

upstream raw materials:

4-methoxy-phenyl-sulphonyl chloride

D-penicillamine methyl ester hydrochloride

Downstream raw materials:

methyl 4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylic acid

(S)-4-(4-Methoxy-benzenesulfonyl)-2,2-dimethyl-[1,4]thiazepane-3-carboxylic acid hydroxyamide

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