(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal

Base Information

Chemical Name:(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal
CAS No.:808154-74-7
Molecular Formula:C₁₈H₂₂F₂N₂O₅S₂
Molecular Weight:448.512
Hs Code.:

Synonyms:(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal

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Chemical Property of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal

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Technology Process of (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal

There total 10 articles about (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal 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: 80.0%

: 808154-72-5
(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone

: 808154-74-7
(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal

Guidance literature:: With boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/j.bmcl.2004.08.050

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 808154-74-7
(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / aq. NaOH / tetrahydrofuran / 20 °C

2: trichloroisocyanuric acid; TEMPO / CH₂Cl₂

3: HMPT; Zn / tetrahydrofuran

4: TFA / CH₂Cl₂

5: Et₃N / dimethylformamide; tetrahydrofuran

6: 85 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

7: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

8: 80 percent / EtSH-BF₃OEt₂ / CH₂Cl₂ / 12 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; chloro-trimethyl-silane; trichloroisocyanuric acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; ethanethiol; zinc; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2004.08.050

Reference yield:

: 60547-92-4
4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

: 808154-74-7
(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)-4-(difluoromethylidene)pyrrolidine-2-carboxaldehyde di(ethylthio)acetal

Guidance literature:: Multi-step reaction with 5 steps

1: (COCl)2; DMF / tetrahydrofuran

2: Et₃N / dimethylformamide; tetrahydrofuran

3: 85 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

4: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

5: 80 percent / EtSH-BF₃OEt₂ / CH₂Cl₂ / 12 h / 20 °C

With chloro-trimethyl-silane; oxalyl dichloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triethylamine; N,N-dimethyl-formamide; ethanethiol; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2004.08.050