ChemicalBook CAS DataBase List CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI)

CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI) synthesis

11synthesis methods

Product Name:CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI)
CAS Number:247068-81-1
Molecular formula:C14H25NO3
Molecular Weight:255.35

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CarbaMic acid, [(1S)-3-Methyl-1-(2-Methylpropyl)-2-oxo-3-butenyl]-, 1,1-diMethylethyl ester (9CI)

247068-81-1
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$19.00/250mg

Yield:247068-81-1 92%

Reaction Conditions:

in diethyl ether at -78; for 2.5 h;

Steps:

The second (right hand) molecular fragment can be made in parallel or in sequence. This procedure involves alkenylating a Weinreb amide of an amino terminal protected amino acid. For example, an amino terminal protected amino acid can be reacted with a reagent (for example, MeNHOMeHCl, EDCl, NMM, HoBt, DMF, 0, 12 h, 80%) to make a Weinreb amide of the carboxyl terminus of the amino acid. Alkenylation is carried out by exposing the Weinreb amide to an alkenylating agent (for example, propen-2-yl lithium) to give an ?','-unsaturated ketone. For example, for an epoxomicin synthesis, Boc-Leu Weinreb amide can be reacted with propen-2-yl lithium to give the corresponding ?','-unsaturated ketone. Propen-2-yl lithium can be generated by reaction of 2-bromopropene with t-butyl lithium in a non-protic solvent (for example, diethyl ether) at low temperature (for example -78 C.), for at least 30 minutes (for example 2.5 hours) to give the ?','-unsaturated ketone in excellent yield (for example, 92%).

References:

US6831099,2004,B1 Location in patent:Page column 13-14