tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Base Information

• Chemical Name: tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS No.: 1325715-38-5
• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 398.502
• Mol file: 1325715-38-5.mol

Synonyms:tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property of tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

There total 7 articles about tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 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: 56.0%

2-(benzyl(tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1030372-40-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (1325715-38-5)

Guidance literature:

2-(benzyl(tert-butoxycarbonyl)amino)-3-phenylpropanoic acid; With (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

N,O-dimethylhydroxylamine*hydrochloride; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.05.123

Reference yield:

benzyl bromide (100-39-0) + Boc-Phe-OH N,O-dimethyl hydroxamate (87694-53-9) → tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (1325715-38-5)

Guidance literature:

Boc-Phe-OH N,O-dimethyl hydroxamate; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

benzyl bromide; In tetrahydrofuran; at 25 ℃; for 24h;

DOI:10.1002/anie.201506881

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → tert-butyl benzyl(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (1325715-38-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hydroxide monohydrate / methanol / 0.33 h / 20 °C

1.2: 1 h

2.1: sodium tetrahydroborate / methanol / 0.5 h

3.1: tetra(n-butyl)ammonium hydroxide / acetonitrile / 0.5 h / 20 °C

3.2: 18 h / 20 °C

4.1: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

4.2: 18 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; lithium hydroxide monohydrate; tetra(n-butyl)ammonium hydroxide; triethylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2011.05.123

upstream raw materials:

2-(benzyl(tert-butoxycarbonyl)amino)-3-phenylpropanoic acid

N,O-dimethylhydroxylamine*hydrochloride

L-phenylalanine

N-benzyl-L-phenylalanine

Downstream raw materials:

N-benzyl-N-(tert-butoxycarbonyl)-L-phenylalaninal

1,5-dibenzyl-1H-imidazol-2-amine hydrochloride

C₁₇H₁₇N₃