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
• Mol file: 135760-76-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(3R,4R)-2-oxo-3-<<(phenylmethoxy)carbonyl>amino>azetidine-4-carboxylic acid (135821-31-7) + methyl iodide (74-88-4) → methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate (135760-76-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 10.5h;

DOI:10.1021/jo00018a035

Reference yield:

methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate (135760-76-8) → (1R,16R)-cyclo-(D-Ala-Ala-N(Me)-Tyr(OMe)-Ala-N-(Me)-(cCHCON(Me)CH)CO) (135789-10-5)

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:

methyl (3R,4R)-1-methyl-2-oxo-3-<<(phenylmethoxy)carbonyl>methylamino>azetidine-4-carboxylate (135760-76-8) → (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 (135760-80-4)

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

upstream raw materials:

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

methyl iodide

Downstream raw materials:

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

(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

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

methyl (3R,4R)-3-<(CBZNH-D-alanyl-L-alanyl-N(Me)-L-tyrosyl(OMe)-L-alanyl)methylamino>-1-methyl-2-oxoazetidine-4-carboxylate