1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one

Base Information

• Chemical Name: 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one
• CAS No.: 1268344-85-9
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 1268344-85-9.mol

Synonyms:1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one

Chemical Property of 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one

There total 1 articles about 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 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: 63.0%

(E)-4-chloro-3-methoxy-but-2-enoic acid methyl ester (110104-60-4,85153-60-2) + (S)-2-amino-2-(4-methoxyphenyl)-1-ethanol (191109-48-5) → 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one (1268344-85-9)

Guidance literature:

(E)-4-chloro-3-methoxy-but-2-enoic acid methyl ester; (S)-2-amino-2-(4-methoxyphenyl)-1-ethanol; In acetonitrile; at 80 ℃; for 0.25h;

With triethylamine; In acetonitrile; at 80 ℃; for 7h;

DOI:10.1002/chem.201002063

Reference yield:

1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one (1268344-85-9) + benzyl bromide (100-39-0) → (S)-5-benzyl-1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one + (S)-5-benzyl-1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one (1268345-08-9)

Guidance literature:

1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

benzyl bromide; In tetrahydrofuran; at -78 ℃; for 7h; optical yield given as %de;

DOI:10.1002/chem.201002063

Reference yield:

1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one (1268344-85-9) → belamide A

Guidance literature:

Multi-step reaction with 7 steps

1.1: tert.-butyl lithium / tetrahydrofuran / -78 °C

1.2: 7 h / -78 °C

2.1: ammonium cerium (IV) nitrate; water / acetonitrile

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 0.5 h / -78 °C

4.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C

5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C

7.1: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C / 735.58 Torr

With n-butyllithium; ammonium cerium (IV) nitrate; palladium 10% on activated carbon; water; hydrogen; tert.-butyl lithium; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

DOI:10.1002/chem.201002063

upstream raw materials:

(E)-4-chloro-3-methoxy-but-2-enoic acid methyl ester

(S)-2-amino-2-(4-methoxyphenyl)-1-ethanol

Downstream raw materials:

(5S)-benzyl-4-methoxy-2,5-dihydropyrrol-2-one

C₂₇H₃₂N₂O₅

C₂₂H₂₄N₂O₃

N-Boc-L-Val-N-Me-L-Val-N-Me-L-Phe-Dpy