3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester

Base Information

• Chemical Name: 3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester
• CAS No.: 339541-45-6
• Molecular Formula: C₂₂H₂₅NO₄S
• Molecular Weight: 399.511

Synonyms:3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester

Chemical Property of 3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester

Chemical Property:

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Technology Process of 3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester

There total 3 articles about 3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester 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: 68.0%

2-(benzyloxycarbonyl-methyl-amino)-thiobenzoic acid S-pyridin-2-yl ester (339541-44-5) + S-tert-butyl thioacetate (999-90-6) → 3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester (339541-45-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

DOI:10.7164/antibiotics.54.109

Reference yield:

2-(benzyloxycarbonyl-methyl-amino)-benzoic acid methyl ester (339541-58-1) → 3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester (339541-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / KOH / H₂O; methanol / 10 h / 65 °C

2: 84 percent / PPh₃P / tetrahydrofuran / 5 h / 20 °C

3: 68 percent / LiN(TMS)2 / tetrahydrofuran / 1 h / -78 - 20 °C

With potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water;

DOI:10.7164/antibiotics.54.109

Reference yield:

2-(Benzyloxycarbonyl-methyl-amino)-benzoic acid (130472-79-6) → 3-[2-(benzyloxycarbonyl-methyl-amino)-phenyl]-3-oxo-thiopropionic acid S-tert-butyl ester (339541-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / PPh₃P / tetrahydrofuran / 5 h / 20 °C

2: 68 percent / LiN(TMS)2 / tetrahydrofuran / 1 h / -78 - 20 °C

With lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.7164/antibiotics.54.109

upstream raw materials:

2-(benzyloxycarbonyl-methyl-amino)-thiobenzoic acid S-pyridin-2-yl ester

S-tert-butyl thioacetate

2-(benzyloxycarbonyl-methyl-amino)-benzoic acid methyl ester

2-(Benzyloxycarbonyl-methyl-amino)-benzoic acid

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