methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate

Base Information

Chemical Name:methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate
CAS No.:135760-76-8
Molecular Formula:C₁₅H₁₈N₂O₅
Molecular Weight:306.318
Hs Code.:

Synonyms:methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate

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Chemical Property of methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate

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Technology Process of methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate

There total 1 articles about methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-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: 84.0%

: 135821-31-7
(3R,4R)-2-oxo-3-<<(phenylmethoxy)carbonyl>amino>azetidine-4-carboxylic acid

: 74-88-4
methyl iodide

: 135760-76-8
methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 10.5h;
DOI:10.1021/jo00018a035

Reference yield:

: 135760-76-8
methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate

: 135789-10-5
(1R,16R)-cyclo-(D-Ala-Ala-N(Me)-Tyr(OMe)-Ala-N-(Me)-(cCHCON(Me)CH)CO)

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / H₂ / Pd/C / tetrahydrofuran / 8 h / 25 °C / 760 Torr

2: 48 percent / DCC, HOBt-H₂O / dimethylformamide / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h

3: 66 percent / LiOH, H₂O / tetrahydrofuran; methanol / 3 h / 25 °C

4: H₂ / 10percent Pd/C / methanol / 8 h / 25 °C / 760 Torr

5: 42 percent / NaHCO₃, diphenyl phosphorazidate / dimethylformamide / 72 h / 25 °C

With lithium hydroxide; diphenyl phosphoryl azide; water; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00018a035

Reference yield:

: 135760-76-8
methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate

: 135760-80-4
(2R,3R)-3-({(S)-2-[(S)-2-{[(S)-2-((R)-2-Amino-propionylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionylamino]-propionyl}-methyl-amino)-1-methyl-4-oxo-azetidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / H₂ / Pd/C / tetrahydrofuran / 8 h / 25 °C / 760 Torr

2: 48 percent / DCC, HOBt-H₂O / dimethylformamide / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h

3: 66 percent / LiOH, H₂O / tetrahydrofuran; methanol / 3 h / 25 °C

4: H₂ / 10percent Pd/C / methanol / 8 h / 25 °C / 760 Torr

With lithium hydroxide; water; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00018a035