tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole

Base Information

• Chemical Name: tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole
• CAS No.: 784191-98-6
• Molecular Formula: C₂₄H₃₀N₂O₆S
• Molecular Weight: 474.578
• Mol file: 784191-98-6.mol

Synonyms:tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole

Chemical Property of tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole

There total 1 articles about tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole 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: 76.0%

O-benzyl carbamate (621-84-1) + Boc-L-Pro-H (69610-41-9,117625-90-8) + Benzenesulfinic acid (618-41-7) → tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole (784191-98-6) + tert-butyl (2S)-2-[(S)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole

Guidance literature:

With magnesium sulfate; In dichloromethane; at 20 ℃;

DOI:10.1021/jo048882y

Reference yield:

ethyl acetate (141-78-6) + tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole (784191-98-6) → tert-butyl (2S)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-ethoxy-3-oxopropyl)tetrahydro-1H-1-pyrrolecarboxylate + tert-butyl (2S)-2-((1R)-1-[(benzyloxy)carbonyl]amino-3-ethoxy-3-oxopropyl)tetrahydro-1H-1-pyrrolecarboxylate (784192-04-7)

Guidance literature:

ethyl acetate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jo048882y

Reference yield:

tert-butyl (2S)-2-[(R)-1-[(benzyloxy)carbonyl]amino-1-(phenylsulfonyl)methyl]tetrahydro-1H-1-pyrrole (784191-98-6) → benzyl N-(1S)-3-hydroxy-1-[(2R)-tetrahydro-1H-2-pyrrolyl]propylcarbamate (784192-07-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 73 percent / CaCl₂; NaBH₄ / tetrahydrofuran / 20 °C

3.1: 85 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; calcium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/jo048882y

upstream raw materials:

O-benzyl carbamate

Boc-L-Pro-H

Benzenesulfinic acid

Downstream raw materials:

tert-butyl (2S)-2-((1R)-1-[(benzyloxy)carbonyl]amino-3-ethoxy-3-oxopropyl)tetrahydro-1H-1-pyrrolecarboxylate

benzyl N-(1S)-3-hydroxy-1-[(2R)-tetrahydro-1H-2-pyrrolyl]propylcarbamate

tert-butyl (2R)-2-((1S)-1-[(benzyloxy)carbonyl]amino-3-hydroxypropyl)tetrahydro-1H-1-pyrrolecarboxylate