methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ⁶-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

Base Information

• Chemical Name: methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ⁶-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate
• CAS No.: 478811-47-1
• Molecular Formula: C₁₆H₁₉N₃O₈S
• Molecular Weight: 413.408

Synonyms:methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ⁶-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

Chemical Property of methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ⁶-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

Chemical Property:

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Technology Process of methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ⁶-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

There total 4 articles about methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ⁶-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate 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: 69.0%

methyl (2S)-4-[(R,S)-[2-(methoxycarbonyl)ethyl]sulfonimidoyl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate (478811-40-4) → methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ6-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate (478811-47-1)

Guidance literature:

With acetic acid; at 50 ℃;

Reference yield:

(N-4-nitrobenzyloxycarbonyl)-L-homocysteine methyl ester (219506-48-6) → methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ6-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate (478811-47-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / K₂CO₃ / methanol / 1 h / 20 °C

2: 91 percent / NaIO₄ / tetrahydrofuran; H₂O

3: 91 percent / O-(mesitylenesulfonyl)hydroxylamine / acetonitrile

4: 69 percent / AcOH / 50 °C

With sodium periodate; mesitylenesulfonylhydroxylamine; potassium carbonate; acetic acid; In tetrahydrofuran; methanol; water; acetonitrile;

Reference yield:

methyl (2S)-4-[(R,S)-[2-(methoxycarbonyl)ethyl]sulfinyl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate (478811-33-5) → methyl (2S)-4-[(1RS)-4,5-dihydro-1,3-dioxo-3H-1λ6-1,2-thiazol-1-yl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate (478811-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / O-(mesitylenesulfonyl)hydroxylamine / acetonitrile

2: 69 percent / AcOH / 50 °C

With mesitylenesulfonylhydroxylamine; acetic acid; In acetonitrile;

upstream raw materials:

methyl (2S)-4-[(R,S)-[2-(methoxycarbonyl)ethyl]sulfonimidoyl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

(N-4-nitrobenzyloxycarbonyl)-L-homocysteine methyl ester

methyl (2S)-4-[2-(methoxycarbonyl)ethylthio]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

methyl (2S)-4-[(R,S)-[2-(methoxycarbonyl)ethyl]sulfinyl]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

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