(2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

Base Information

Chemical Name:(2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal
CAS No.:745014-24-8
Molecular Formula:C₂₄H₃₇N₃O₇S₂
Molecular Weight:543.706
Hs Code.:

Synonyms:(2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

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Chemical Property of (2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

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Technology Process of (2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

There total 6 articles about (2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal 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: 60.0%

: 105089-88-1
(2S)-2-[di(ethylsulfanyl)methyl]tetrahydro-1H-pyrrole

: 757189-86-9
4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoic acid

: 745014-24-8
(2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; water; at 20 ℃; for 24h;
DOI:10.1016/j.bmc.2004.06.013

Reference yield:

: 39684-80-5
2-(tert-butoxycarbonylamino)ethyl bromide

: 140647-02-5
(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal

: 745014-24-8
(2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1016/j.bmcl.2004.04.087

Reference yield:

: 61032-41-5
methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate

: 745014-24-8
(2S)-N-[4-(N-t-butoxycarbonyl)aminoethoxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl thioacetal

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / EtSH; BF₃*Et₂O / CH₂Cl₂ / 20 °C

2: 85 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

3: 80 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O; methanol / 4 h / 20 °C

4: 60 percent / EDCI; HOBt / CH₂Cl₂; H₂O / 24 h / 20 °C

With lithium hydroxide; boron trifluoride diethyl etherate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethanethiol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2004.06.013