(2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Base Information

• Chemical Name: (2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
• CAS No.: 135347-23-8
• Molecular Formula: C₂₅H₂₈N₂O₇S
• Molecular Weight: 500.573
• Mol file: 135347-23-8.mol

Synonyms:(2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Chemical Property of (2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

There total 1 articles about (2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl 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: 17.0%

3-methylbenzo[d]isothiazole-1,1-dioxide (34989-82-7) + benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3) → (2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (135347-23-8) + (2S,4S)-4-((S)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (135347-24-9)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) -78 deg C -> -50 deg C, 1 h;

DOI:10.1016/S0040-4020(97)00666-2

Reference yield: 40.0%

(2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (135347-23-8) → 3-methylbenzo[d]isothiazole-1,1-dioxide (34989-82-7) + benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; 1.) -78 deg C, 30 min, 2.) -78 deg C -> room temperature, 2 h;

DOI:10.1016/S0040-4020(97)00666-2

Reference yield:

(2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (135347-23-8) → (2S,4S)-4-Benzyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 38 percent / LiHMDS / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C -> room temperature, 2 h

2: 45 percent / LiHMDS / tetrahydrofuran / 1 h / -78 °C

3: 69 percent / LiHMDS / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C -> room temperature, 25 h, 3.) room temperature, 1 h

4: 58 percent / H₂ / Pd/C / ethyl acetate / 15 h / Ambient temperature

With hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/S0040-4020(97)00666-2

upstream raw materials:

3-methylbenzo[d]isothiazole-1,1-dioxide

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Downstream raw materials:

3-methylbenzo[d]isothiazole-1,1-dioxide

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

(2S,4S)-5-Oxo-4-[(S)-phenyl-(toluene-4-sulfonylamino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

(2S,4S)-5-Oxo-4-[(R)-phenyl-(toluene-4-sulfonylamino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester