2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethanone

Base Information

• Chemical Name: 2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethanone
• CAS No.: 131700-92-0
• Molecular Formula: C₂₃H₂₀N₂O₃S
• Molecular Weight: 404.489

Synonyms:2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethanone

Chemical Property of 2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethanone

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Technology Process of 2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethanone

There total 8 articles about 2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethanone 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:

methyl N-(diphenylmethylene)glycinate (81167-39-7) + (R)-3-methyl-2,3-dihydrobenzo[d]isothiazoline 1,1-dioxide (130973-53-4) → 2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-ethanone (131700-92-0)

Guidance literature:

With trimethylaluminum; W_. Oppolzer, R_. Moretti, S_. Thomi, Tetrahedron Lett_. 1989, 30, 6009;

DOI:10.1016/S0040-4039(00)97794-3

Reference yield:

1-((R)-3-Methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-propan-1-one (131700-89-5) → 2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-ethanone (131700-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) diethylboryl triflate, EtN(iPr)2 / 1.) CH₂Cl₂, hexane, -5 deg C, 0.5 h, 2.) -78 deg C, 20 min

2: 92 percent / aq. H₂O₂ (30 percent), LiOH*H₂O / tetrahydrofuran; H₂O / 2 h / 0 °C

3: Me₃Al / W_. Oppolzer, R_. Moretti, S_. Thomi, Tetrahedron Lett_. 1989, 30, 6009

With lithium hydroxide; dihydrogen peroxide; trimethylaluminum; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)97794-3

Reference yield:

(S)-2-Methyl-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-3-phenyl-propane-1,3-dione (131700-99-7) → 2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-ethanone (131700-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NaHB(sBu)3 / tetrahydrofuran / 0.5 h / -78 °C

2: aq. H₂O₂ (30 percent), LiOH*H₂O / tetrahydrofuran; H₂O / 0 °C

3: Me₃Al / W_. Oppolzer, R_. Moretti, S_. Thomi, Tetrahedron Lett_. 1989, 30, 6009

With lithium hydroxide; dihydrogen peroxide; trimethylaluminum; sodium tri-sec-butylborohydride; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)97794-3

upstream raw materials:

methyl N-(diphenylmethylene)glycinate

(R)-3-methyl-2,3-dihydrobenzo[d]isothiazoline 1,1-dioxide

1-((R)-3-Methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-propan-1-one

(2R,3S)-3-Hydroxy-2,4-dimethyl-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-pentan-1-one

Downstream raw materials:

(S)-2-(Benzhydrylidene-amino)-1-((R)-3-methyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-3-phenyl-propan-1-one

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