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

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Chemical Name:(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone
CAS No.:808154-72-5
Molecular Formula:C₂₅H₂₈F₂N₂O₅S₂
Molecular Weight:538.637
Hs Code.:

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

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Chemical Property of (4-Benzyloxy-5-methoxy-2-nitro-phenyl)-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone

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Technology Process of (4-Benzyloxy-5-methoxy-2-nitro-phenyl)-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone

There total 10 articles about (4-Benzyloxy-5-methoxy-2-nitro-phenyl)-[(S)-2-(bis-ethylsulfanyl-methyl)-4-difluoromethylene-pyrrolidin-1-yl]-methanone 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: 90.0%

: 75-08-1
ethanethiol

: 808154-70-3
(S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-4-difluoromethylene-pyrrolidine-2-carbaldehyde

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

Guidance literature:: With chloro-trimethyl-silane; In chloroform; at 20 ℃; for 24h;
DOI:10.1016/j.bmcl.2004.08.050

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: 64154-78-5
4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride

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

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N / dimethylformamide; tetrahydrofuran

2: 85 percent / DIBAL-H / CH₂Cl₂ / 0.75 h / -78 °C

3: 90 percent / TMSCl / CHCl₃ / 24 h / 20 °C

With chloro-trimethyl-silane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2004.08.050