(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester
• CAS No.: 761435-76-1
• Molecular Formula: C₂₁H₃₁NO₇S
• Molecular Weight: 441.546
• Mol file: 761435-76-1.mol

Synonyms:(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester

Chemical Property of (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester

There total 8 articles about (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid tert-butyl ester (761435-74-9) → (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester (761435-76-1)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield:

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid (71449-08-6) → (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester (761435-76-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 60 percent / BH₃ / tetrahydrofuran

2: 97 percent / TEA / CH₂Cl₂

3: 60 percent / NaH / dimethylformamide / 20 °C

4: 95 percent / K₂CO₃ / dimethylformamide

5: 90 percent / LDA / tetrahydrofuran

6: 90 percent / Oxone / methanol; H₂O

7: 36 percent / O₃; P(OMe)3 / CH₂Cl₂

8: 99 percent / H₂ / Pd-C / methanol

9: 97 percent / NaHCO₃ / H₂O; tetrahydrofuran

With Oxone; TEA; borane; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; lithium diisopropyl amide; phosphorous acid trimethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield:

(R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester (146398-01-8) → (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester (761435-76-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / TEA / CH₂Cl₂

2: 60 percent / NaH / dimethylformamide / 20 °C

3: 95 percent / K₂CO₃ / dimethylformamide

4: 90 percent / LDA / tetrahydrofuran

5: 90 percent / Oxone / methanol; H₂O

6: 36 percent / O₃; P(OMe)3 / CH₂Cl₂

7: 99 percent / H₂ / Pd-C / methanol

8: 97 percent / NaHCO₃ / H₂O; tetrahydrofuran

With Oxone; TEA; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; lithium diisopropyl amide; phosphorous acid trimethyl ester; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.049

upstream raw materials:

di-tert-butyl dicarbonate

(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid tert-butyl ester

(R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid

Downstream raw materials:

(2R,3S)-2-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-pyrrolidine-1,3-dicarboxylic acid di-tert-butyl ester