(S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester

Base Information

Chemical Name:(S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester
CAS No.:78246-52-3
Molecular Formula:C₂₀H₁₆N₂O₆
Molecular Weight:380.357
Hs Code.:

Synonyms:(S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester

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Chemical Property of (S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester

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Technology Process of (S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester

There total 6 articles about (S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester 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: 43.0%

: 64232-07-1,64253-60-7,68749-65-5,78246-51-2
(4-Benzyloxy-phenyl)-[(S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-acetic acid methyl ester

: 71336-84-0
methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate

: 78246-52-3
(S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; acetic acid; for 2h;
DOI:10.1021/ja00342a047

Reference yield:

: 78246-50-1
methyl (L)-N^α-phthaloylseryl-(D)-p-benzyloxyphenylglycinate

: 78246-52-3
(S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature; influence of reagents amount

2: H₂ / palladium on carbon / methanol; acetic acid / 2 h

With hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid;
DOI:10.1021/ja00342a047

Reference yield:

: 29588-89-4
(2S)-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropanoic acid

: 78246-52-3
(S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 58 percent / 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride / tetrahydrofuran; CH₂Cl₂ / 2.5 h / Ambient temperature

2: tetra-n-butylammonium fluoride, N,N-sulfuryl diimidazole / tetrahydrofuran

3: 1.) tetra-n-butylammonium fluoride, N,N-sulfuryl diimidazole, 2.) H₂ / 2.) 10percent Pd/C / 1.) THF, overnight, 2.) methanol/acetic acid, overnight

With tetrabutyl ammonium fluoride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N`-sulfuryldiimidazole; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.1139/v85-593