methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

Base Information

Chemical Name:methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate
CAS No.:905281-21-2
Molecular Formula:C₂₂H₃₁ClN₂O₇S
Molecular Weight:503.016
Hs Code.:

Synonyms:methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

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Chemical Property of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

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Technology Process of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

There total 5 articles about methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate 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: 48.0%

: 850317-92-9
methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)-3-chlorophenyl]propanoate

: 905281-21-2
methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

: methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5R)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1021/jm0600904

Reference yield:

: 850317-90-7
methyl (2S)-3-(4-amino-3-chlorophenyl)-2-[(tert-butoxycarbonyl)amino]propanoate

: 905281-21-2
methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: aq. hydrochloric acid; sodium nitrite / 0.5 h / 0 °C

1.2: 2.1 g / aq. potassium iodide / 0.67 h / 20 - 35 °C

2.1: 64 percent / tetra-N-butylammonium chloride; palladium acetate; triethylamine / dimethylformamide / 2 h / 65 °C

3.1: 48 percent / lithium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C

With hydrogenchloride; lithium borohydride; tetrabutyl-ammonium chloride; palladium diacetate; triethylamine; sodium nitrite; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: Heck reaction;
DOI:10.1021/jm0600904

Reference yield:

: 850317-91-8
methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-iodophenyl)propanoate

: 905281-21-2
methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(5S)-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)]-3-chlorophenyl}propanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 64 percent / tetra-N-butylammonium chloride; palladium acetate; triethylamine / dimethylformamide / 2 h / 65 °C

2: 48 percent / lithium tetrahydroborate / tetrahydrofuran / 0.5 h / 20 °C

With lithium borohydride; tetrabutyl-ammonium chloride; palladium diacetate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Heck reaction;
DOI:10.1021/jm0600904