(2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester
• CAS No.: 1446911-24-5
• Molecular Formula: C₃₃H₄₁N₃O₈S
• Molecular Weight: 639.77
• Mol file: 1446911-24-5.mol

Synonyms:(2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester

Chemical Property of (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester

There total 5 articles about (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic 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: 55.0%

(2S,4S)-4-iodo-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester (928065-03-6) + ((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-oxo-acetaldehyde O-benzyl-oxime → (2S,4R)-4-[(1R)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester (1446911-14-3) + (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester (1446911-24-5)

Guidance literature:

With triethyl borane; In hexane; dichloromethane; at 20 ℃; for 1h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2013.06.006

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,4R)-4-[(1R)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester (1446911-14-3) + (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester (1446911-24-5)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate / water; tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: sulfuric acid / 10 h / Reflux

3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 17 h / 20 °C / Inert atmosphere

4: triethyl borane / hexane; dichloromethane / 1 h / 20 °C / Inert atmosphere

With triethyl borane; sulfuric acid; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 3: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2013.06.006

Reference yield:

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → (2S,4R)-4-[(1R)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester (1446911-14-3) + (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester (1446911-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 10 h / Reflux

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 17 h / 20 °C / Inert atmosphere

3: triethyl borane / hexane; dichloromethane / 1 h / 20 °C / Inert atmosphere

With triethyl borane; sulfuric acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; toluene; 2: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2013.06.006

upstream raw materials:

(2S,4S)-4-iodo-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester

benzyl chloroformate

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate