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

Base Information

• Chemical Name: (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 761435-74-9
• Molecular Formula: C₁₆H₂₃NO₅S
• Molecular Weight: 341.428
• Mol file: 761435-74-9.mol

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

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

There total 8 articles about (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid 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: 99.0%

(2S,3R)-4-(4-Benzyloxy-benzenesulfonyl)-3-benzyloxycarbonylamino-2-(2-oxo-ethyl)-butyric acid tert-butyl ester (761435-72-7) → (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid tert-butyl ester (761435-74-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

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-3-carboxylic acid tert-butyl ester (761435-74-9)

Guidance literature:

Multi-step reaction with 7 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

With Oxone; TEA; hydrogen; sodium hydride; 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:

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid (71449-08-6) → (2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-pyrrolidine-3-carboxylic acid tert-butyl ester (761435-74-9)

Guidance literature:

Multi-step reaction with 8 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

With Oxone; TEA; borane; hydrogen; sodium hydride; 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:

(2S,3R)-4-(4-Benzyloxy-benzenesulfonyl)-3-benzyloxycarbonylamino-2-(2-oxo-ethyl)-butyric 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

3-benzyloxycarbonylamino-4-methanesulfonyloxy-butyric acid tert-butyl ester

Downstream raw materials:

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

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