Methyl chloroformate → HCID 14651533, compound

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[CH2:4][C@H:5]([CH3:10])[CH2:6][C:7]([OH:9])=[O:8].Cl[C:13]([O:15][CH3:16])=[O:14]>>[CH3:1][O:2][C:3](=[O:11])[CH:4]([C:13]([O:15][CH3:16])=[O:14])[C@H:5]([CH3:10])[CH2:6][C:7]([OH:9])=[O:8]

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 6999733(R)-1-Methyl hydrogen 3-methylglutarate

Product 1

HCID 14651533HCID 14651533, compound

Procedure

Scheme 1 illustrates an exemplary method for making a compound of the formula 1.3. Starting from (R)-5-methoxy-3-methyl-5-oxopentanoic acid, reaction with methyl chloroformate gives (R)-5-methoxy-4-(methoxycarbonyl)-3-methyl-5-oxopentanoic acid, which can be esterified with, for example, trimethylsilyl chloride and methanol to give compound 1.3, (R)-trimethyl 2-methylpropane-1,1,3-tricarboxylate.

Sources & evidence

ORD record: ord-58fb4dbe6f734f54bf72d38c347f879f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309204B2

Reaction notes

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