(S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

Base Information

Chemical Name:(S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate
CAS No.:1381860-50-9
Molecular Formula:C₂₃H₂₀FNO₄
Molecular Weight:393.415
Hs Code.:

Synonyms:(S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

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Chemical Property of (S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

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Technology Process of (S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

There total 3 articles about (S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate 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: 93.0%

: 1374450-07-3
tert-butyl 3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

: 1381860-32-7
C₁₅H₁₆FNO₃

: 1381860-50-9
(S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

Guidance literature:: With (2S,3R)-2-{3-[3,5-bis(trifluoromethyl)phenyl]thioureido}-3-[(tert-butyldiphenylsilyl)oxy]-N-{(S)-quinolin-4-yl-[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methyl}butanamide; In toluene; at 20 ℃; for 36h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ja303115m

Reference yield:

: 129881-51-2,75724-95-7
acid chloride of 1-oxo-1,3-dihydroisobenzofuran-3-carboxylic acid

: 1381860-50-9
(S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 20 °C

2: (2S,3R)-2-{3-[3,5-bis(trifluoromethyl)phenyl]thioureido}-3-[(tert-butyldiphenylsilyl)oxy]-N-{(S)-quinolin-4-yl-[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methyl}butanamide / toluene / 36 h / 20 °C / Inert atmosphere

With dmap; (2S,3R)-2-{3-[3,5-bis(trifluoromethyl)phenyl]thioureido}-3-[(tert-butyldiphenylsilyl)oxy]-N-{(S)-quinolin-4-yl-[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methyl}butanamide; triethylamine; In dichloromethane; toluene;
DOI:10.1021/ja303115m

Reference yield:

: 708-14-5,62283-01-6,99266-05-4
phthalide-3-carboxylic acid

: 1381860-50-9
(S,Z)-tert-butyl 1-(2-cyano-3-(3-fluorophenyl)allyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 - 20 °C

2: dmap; triethylamine / dichloromethane / 20 °C

3: (2S,3R)-2-{3-[3,5-bis(trifluoromethyl)phenyl]thioureido}-3-[(tert-butyldiphenylsilyl)oxy]-N-{(S)-quinolin-4-yl-[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methyl}butanamide / toluene / 36 h / 20 °C / Inert atmosphere

With dmap; oxalyl dichloride; (2S,3R)-2-{3-[3,5-bis(trifluoromethyl)phenyl]thioureido}-3-[(tert-butyldiphenylsilyl)oxy]-N-{(S)-quinolin-4-yl-[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methyl}butanamide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja303115m