(R)-3-[4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one

Base Information

• Chemical Name: (R)-3-[4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one
• CAS No.: 268209-34-3
• Molecular Formula: C₁₅H₁₆FN₃O₄S₂
• Molecular Weight: 385.44

Synonyms:(R)-3-[4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one

Chemical Property of (R)-3-[4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one

Chemical Property:

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Technology Process of (R)-3-[4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one

There total 3 articles about (R)-3-[4-(1,1-Dioxo-1λ⁶-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one 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:

carbon disulfide (75-15-0,12122-00-8) + (S)-5-Aminomethyl-3-[4-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-3-fluoro-phenyl]-oxazolidin-2-one (216869-41-9) → (R)-3-[4-(1,1-Dioxo-1λ6-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one (268209-34-3)

Guidance literature:

With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1248/cpb.49.361

Reference yield:

(R)-<3-<3-fluoro-4-(4-thiomorpholinyl)phenyl>-2-oxo-5-oxazolidinyl>methyl azide (168828-74-8) → (R)-3-[4-(1,1-Dioxo-1λ6-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one (268209-34-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 86 percent / methyl morpholine N-oxide; osmium tetroxide / H₂O; acetone / 0.17 h / 20 °C

2.1: triphenylphosphine; H₂O / tetrahydrofuran / 11 h / 40 °C

3.1: Et₃N / tetrahydrofuran / 4 h / 0 °C

3.2: ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C

With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; water; acetone;

DOI:10.1248/cpb.49.353

Reference yield:

(R)-5-azidomethyl-3-[4-(1,1-dioxo-4-thiomorpholinyl)-3-fluorophenyl]oxazolidine-2-one (268208-97-5) → (R)-3-[4-(1,1-Dioxo-1λ6-thiomorpholin-4-yl)-3-fluoro-phenyl]-5-isothiocyanatomethyl-oxazolidin-2-one (268209-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine; H₂O / tetrahydrofuran / 11 h / 40 °C

2.1: Et₃N / tetrahydrofuran / 4 h / 0 °C

2.2: ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C

With water; triethylamine; triphenylphosphine; In tetrahydrofuran;

DOI:10.1248/cpb.49.353

upstream raw materials:

carbon disulfide

(S)-5-Aminomethyl-3-[4-(1,1-dioxo-1λ⁶-thiomorpholin-4-yl)-3-fluoro-phenyl]-oxazolidin-2-one

(R)-<3-<3-fluoro-4-(4-thiomorpholinyl)phenyl>-2-oxo-5-oxazolidinyl>methyl azide

(R)-5-azidomethyl-3-[4-(1,1-dioxo-4-thiomorpholinyl)-3-fluorophenyl]oxazolidine-2-one

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