N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide

Base Information

• Chemical Name: N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide
• CAS No.: 377779-93-6
• Molecular Formula: C₂₂H₂₇N₃O₂
• Molecular Weight: 365.475
• Mol file: 377779-93-6.mol

Synonyms:N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide

Chemical Property of N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide

There total 6 articles about N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide 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: 72.0%

(2S)-2-{[(1R)-2-hydroxy-1-phenylethyl]amino}-3-methyl-3-(1-methyl-1H-indole-3-yl)butanenitrile (377779-91-4) → N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide (377779-93-6)

Guidance literature:

With dihydrogen peroxide; potassium carbonate; dimethyl sulfoxide; In methanol; at 45 ℃; for 6h;

DOI:10.1021/jo0104882

Reference yield:

D-2-phenylglycinol (56613-80-0) → N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide (377779-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Sc(OTf)3 / CH₂Cl₂ / 1 h / 20 °C

1.2: 81 percent / CH₂Cl₂ / 0 - 20 °C

2.1: 72 percent / K₂CO₃; DMSO; aq. H₂O₂ / methanol / 6 h / 45 °C

With dihydrogen peroxide; potassium carbonate; dimethyl sulfoxide; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane;

DOI:10.1021/jo0104882

Reference yield:

(±)-methyl 2-(1-methyl-1H-indol-3-yl)propanoate (72228-40-1) → N-[(1'R)-2'-hydroxy-1'-phenylethyl]-(2S)-2-amino-3-methyl-3-(1-methylindol-3-yl)butyramide (377779-93-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -78 - 0 °C / Inert atmosphere

1.2: 3 h / -78 - 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; hexane; diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide / dichloromethane / 1 h / 25 °C / Molecular sieve

4.1: toluene / 1.5 h / Reflux; Inert atmosphere; Dean-Stark

4.2: 96 h / 0 - 25 °C / Inert atmosphere

5.1: potassium carbonate; dihydrogen peroxide / water; methanol; dimethyl sulfoxide / 1.5 h / 0 - 45 °C

With dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;

upstream raw materials:

(2S)-2-{[(1R)-2-hydroxy-1-phenylethyl]amino}-3-methyl-3-(1-methyl-1H-indole-3-yl)butanenitrile

D-2-phenylglycinol

(±)-methyl 2-(1-methyl-1H-indol-3-yl)propanoate

methyl α,α,1-trimethyl-1H-indole-3-acetate