O-tert-butyl (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate

Base Information

• Chemical Name: O-tert-butyl (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate
• CAS No.: 1408283-01-1
• Molecular Formula: C₂₂H₂₈FN₃O₅S
• Molecular Weight: 465.546

Synonyms:O-tert-butyl (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate

Chemical Property of O-tert-butyl (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate

Chemical Property:

Purity/Quality:

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Technology Process of O-tert-butyl (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate

There total 5 articles about O-tert-butyl (R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate 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: 63.0%

(R)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enoic acid (1408282-93-8) + O-(tert-butyl)hydroxylamine hydrochloride (39684-28-1) → O-tert-butyl (R)-N2-(4-methoxyphenylsulfonyl)-N2-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate (1408283-01-1)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmc.2015.03.078

Reference yield:

4-methoxy-phenyl-sulphonyl chloride (98-68-0) → O-tert-butyl (R)-N2-(4-methoxyphenylsulfonyl)-N2-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate (1408283-01-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 48 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Sealed tube

4: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With 4-methyl-morpholine; pyridine; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2015.03.078

Reference yield:

tert-butyl (R)-(+)-2-amino-4-fluoropent-4-enoate (247122-85-6) → O-tert-butyl (R)-N2-(4-methoxyphenylsulfonyl)-N2-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamate (1408283-01-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 48 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Sealed tube

4: benzotriazol-1-ol; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With 4-methyl-morpholine; pyridine; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2015.03.078

upstream raw materials:

4-methoxy-phenyl-sulphonyl chloride

tert-butyl (R)-N-(4-methoxyphenylsulfonyl)-γ-fluoro-α-aminopent-4-enoate

tert-butyl (R)-(+)-2-amino-4-fluoropent-4-enoate

tert-butyl (R)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enoate

Downstream raw materials:

(R)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-amino-4-fluoropent-4-enehydroxamic acid

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