(3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester

Base Information

• Chemical Name: (3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester
• CAS No.: 443149-76-6
• Molecular Formula: C₂₂H₃₆N₂O₃
• Molecular Weight: 376.539
• Mol file: 443149-76-6.mol

Synonyms:(3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester

Chemical Property of (3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester

There total 3 articles about (3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic 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: 42.0%

L-phenylalanine methylamide (35373-92-3) + (3R)-3-bromomethyl-5-methylhexanoic acid tert-butyl ester (443149-75-5) → (3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester (443149-76-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 144h;

DOI:10.1021/jo0110698

Reference yield:

(R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate (144287-83-2) → (3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester (443149-76-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / lithium borohydride; MeOH / diethyl ether / 1.5 h / 0 °C

2: 89 percent / PPh₃; CBr₄ / CH₂Cl₂ / 2 h / 20 °C

3: 42 percent / tetrabutylammonium iodide; potassium carbonate / dimethylformamide / 144 h / 60 °C

With methanol; lithium borohydride; carbon tetrabromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0110698

Reference yield:

(3R)-3-hydroxymethyl-5-methylhexanoic acid tert-butyl ester (181289-32-7) → (3R)-5-methyl-3-[(1S)-(1-methylcarbamoyl-2-phenylethylamino)methyl]hexanoic acid tert-butyl ester (443149-76-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / PPh₃; CBr₄ / CH₂Cl₂ / 2 h / 20 °C

2: 42 percent / tetrabutylammonium iodide; potassium carbonate / dimethylformamide / 144 h / 60 °C

With carbon tetrabromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0110698

upstream raw materials:

L-phenylalanine methylamide

(3R)-3-bromomethyl-5-methylhexanoic acid tert-butyl ester

(R)-tert-butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-methylhexanoate

(3R)-3-hydroxymethyl-5-methylhexanoic acid tert-butyl ester

Downstream raw materials:

(2R)-(2-hydroxycarbamoylmethyl-4-methylpentyl)-(1S)-(1-methylcarbamoyl-2-phenylethyl)carbamic acid benzyl ester

(3R)-3-{[benzyloxycarbonyl-(1S)-(1-methylcarbamoyl-2-phenylethyl)amino]methyl}-5-methylhexanoic acid

(3R)-3-{[benzyloxycarbonyl-(1S)-(1-methylcarbamoyl-2-phenylethyl)amino]methyl}-5-methylhexanoic acid tert-butyl ester