Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid

Base Information

• Chemical Name: Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid
• CAS No.: 116652-76-7
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.299
• Mol file: 116652-76-7.mol

Synonyms:Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid

Chemical Property of Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid

There total 8 articles about Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid 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: 98.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + methyl (2R)-3-(benzyloxy)-2-methylpropanoate (56850-58-9,59965-24-1,74924-27-9,112068-34-5) → (2R)-3-benzyloxy-N-methoxy-N-methyl-2-methylpropanamide (116652-76-7)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; toluene; at -15 ℃; for 0.833333h; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.012

Reference yield: 96.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + methyl (S)-3-benzyloxy-2-methylpropanoate (74924-27-9) → Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid (116652-76-7)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; at -5 ℃; for 1h;

DOI:10.1016/S0040-4020(98)83050-0

Reference yield: 89.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (-)-(R)-3-benzyloxy-2-methylpropionic acid (88729-00-4) → (2R)-3-benzyloxy-N-methoxy-N-methyl-2-methylpropanamide (116652-76-7)

Guidance literature:

(-)-(R)-3-benzyloxy-2-methylpropionic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 10 - 15 ℃; for 1h; Large scale;

N,O-dimethylhydroxylamine*hydrochloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; Large scale;

upstream raw materials:

3-hydroxy-(2S)-methylpropionate

O-benzyl 2,2,2-trichloroacetimidate

N,O-dimethylhydroxylamine*hydrochloride

methyl (S)-3-benzyloxy-2-methylpropanoate

Downstream raw materials:

(R)-1-(benzyloxy)-2-methylpentan-3-one

(2R)-1-benzyloxy-2-methylhexan-3-one

(3S,4S,5S,6R)-7-benzyloxy-4-ethyl-2,6-dimethylhept-1-ene-3,5-diol

C₂₆H₄₁BO₂

Refernces

• 1、 -. "(3R)-2-iodo-4-benzyloxy-3-methyl-1-ene compound as well as preparation method and application thereof". Paragraph 0043; 0044; 0045. . Retrieved 2019/08/02.
• 2、 Premraj, Rajaratnam,McLeod, Malcolm D.,Simpson, Gregory W.,Banwell, Martin G.. "A total synthesis of herboxidiene methyl ester". . p. 2949 - 2976. Retrieved 2013/02/21.