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

Base Information

• Chemical Name: methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate
• CAS No.: 71336-84-0
• Molecular Formula: C₂₀H₁₆N₂O₆
• Molecular Weight: 380.357

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

Chemical Property of methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate

Chemical Property:

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Technology Process of methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate

There total 9 articles about methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate 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%

methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate (64232-07-1) → methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate (71336-84-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1248/cpb.35.3985

Reference yield: 43.0%

(4-Benzyloxy-phenyl)-[(S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-acetic acid methyl ester (64232-07-1,64253-60-7,68749-65-5,78246-51-2) → methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate (71336-84-0) + (S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester (78246-52-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; for 2h;

DOI:10.1021/ja00342a047

Reference yield:

N-phthaloyl-L-serine (29588-89-4) → methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate (71336-84-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1-hydroxybenzotriazole hydrate, 2.) dicyclohexylcarbodiimide / 1.) DMF, 0 deg C, 15 min, 2.) 0 deg C (1 h) , room temperature, 1 h

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

3: 43 percent / H₂ / palladium on carbon / methanol; acetic acid / 2 h

With hydrogen; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid;

DOI:10.1021/ja00342a047

upstream raw materials:

methyl (3R,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-benzyloxyphenyl)acetate

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

N-phthaloyl-L-serine

methyl (L)-N^α-phthaloylseryl-(D)-p-benzyloxyphenylglycinate

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