(S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester

Base Information

• Chemical Name: (S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester
• CAS No.: 219507-24-1
• Molecular Formula: C₁₈H₂₃N₃O₈S
• Molecular Weight: 441.462

Synonyms:(S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester

Chemical Property of (S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester

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Technology Process of (S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester

There total 8 articles about (S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ⁶-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl 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: 27.5%

methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate (219507-06-9) → (S)-4-((1R,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ6-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester (219507-08-1) + (S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ6-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester (219507-24-1)

Guidance literature:

With dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; water; at 0 ℃; for 3h;

DOI:10.1016/S0968-0896(98)00142-4

Reference yield:

(4R,5S)-3-((S)-2-Iodomethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one (219506-97-5) → (S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ6-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester (219507-24-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / K₂CO₃ / dimethylformamide / 1 h / 60 °C

2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 24 h / 25 °C

3: 100 percent / O-mesitylenesulfonylhydroxylamine / acetonitrile / Ambient temperature

4: 27.5 percent / K₂CO₃, H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

With sodium periodate; dihydrogen peroxide; mesitylenesulfonylhydroxylamine; potassium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(98)00142-4

Reference yield:

(4R,5S)-3-((R)-2-Hydroxymethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one (219506-89-5) → (S)-4-((1S,4S)-4-Ethyl-1,3-dioxo-4,5-dihydro-3H-1λ6-isothiazol-1-yl)-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester (219507-24-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / Et₃N / CH₂Cl₂

2: 84 percent / NaI / acetone / Heating

3: 100 percent / K₂CO₃ / dimethylformamide / 1 h / 60 °C

4: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 24 h / 25 °C

5: 100 percent / O-mesitylenesulfonylhydroxylamine / acetonitrile / Ambient temperature

6: 27.5 percent / K₂CO₃, H₂O₂ / tetrahydrofuran; H₂O / 3 h / 0 °C

With sodium periodate; dihydrogen peroxide; mesitylenesulfonylhydroxylamine; potassium carbonate; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0968-0896(98)00142-4

upstream raw materials:

methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate

(4R,5S)-3-((S)-2-Iodomethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one

(4R,5S)-3-((R)-2-Hydroxymethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one

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

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