N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide

Base Information

• Chemical Name: N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide
• CAS No.: 204129-61-3
• Molecular Formula: C₁₇H₂₆N₂O₇S₂
• Molecular Weight: 434.535

Synonyms:N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide

Chemical Property of N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide

There total 11 articles about N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide 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:

6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylic acid chloride → N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide (204129-61-3)

Guidance literature:

With hydroxylamine; triethylamine; In tetrahydrofuran; dichloromethane; at 20 ℃;

DOI:10.1021/jm990330y

Reference yield:

3,3-dimethyl-D-cysteine (52-67-5) → N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide (204129-61-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 2 N aq. NaOH / ethanol / 20 °C

2: Et₃N / dioxane; H₂O / 18 h / 20 °C

3: methanol; diethyl ether

4: 1 N aq. HCl / tetrahydrofuran / 20 °C

5: 82 percent / Et₃N; (dimethylamino)pyridine / CH₂Cl₂ / 20 °C

6: 71 percent / NaI; i-Pr₂NEt / 1,2-dimethoxy-ethane / 4 h / Heating

7: 78 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

8: 86 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

9: 93 percent / LiI; pyridine / 3 h / Heating

10: oxalyl chloride, DMF / CH₂Cl₂ / 0.5 h / 20 °C

11: aq. NH₂OH; Et₃N / tetrahydrofuran; CH₂Cl₂ / 20 °C

With pyridine; hydrogenchloride; dmap; sodium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; hydroxylamine; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; sodium iodide; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; 1: Alkylation / 2: sulfonylation / 3: Esterification / 4: Hydrolysis / 5: silylation / 6: Alkylation / 7: desilylation / 8: Cyclization / 9: demethylation / 10: Chlorination / 11: Acylation;

DOI:10.1021/jm990330y

Reference yield:

(S)-2-Amino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethylsulfanyl)-3-methyl-butyric acid → N-hydroxy-6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxamide (204129-61-3)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N / dioxane; H₂O / 18 h / 20 °C

2: methanol; diethyl ether

3: 1 N aq. HCl / tetrahydrofuran / 20 °C

4: 82 percent / Et₃N; (dimethylamino)pyridine / CH₂Cl₂ / 20 °C

5: 71 percent / NaI; i-Pr₂NEt / 1,2-dimethoxy-ethane / 4 h / Heating

6: 78 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

7: 86 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

8: 93 percent / LiI; pyridine / 3 h / Heating

9: oxalyl chloride, DMF / CH₂Cl₂ / 0.5 h / 20 °C

10: aq. NH₂OH; Et₃N / tetrahydrofuran; CH₂Cl₂ / 20 °C

With pyridine; hydrogenchloride; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydroxylamine; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; sodium iodide; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; 1: sulfonylation / 2: Esterification / 3: Hydrolysis / 4: silylation / 5: Alkylation / 6: desilylation / 7: Cyclization / 8: demethylation / 9: Chlorination / 10: Acylation;

DOI:10.1021/jm990330y

upstream raw materials:

3,3-dimethyl-D-cysteine

methyl 6(S)-methoxymethyl-4-[(4-methoxyphenyl)sulfonyl]-2,2-dimethyl-hexahydro-1,4-thiazepine-3(S)-carboxylate

methyl 2(S)-N-[(4-methoxyphenyl)sulfonyl]-S-(2,3-dihydroxypropyl)-D-penicillamine

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

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