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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1908646Generated: October 28, 2026

Bromopinacolone → (S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester

https://huagongshe.com/reaction/1908646

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBromopinacoloneHCID 21642—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantHCID 178501468HCID 178501468—
SolventDimethylformamideHCID 6228—
Product(S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl esterHCID 66920060—

Reaction Steps

Crude (S)-2-[(5-Hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester (44 g) was dissolved in DMF and treated with 12.2 g potassium tert-butoxide and 14.7 ml 1-bromopinacolone. After 2 h the solvent was removed in vacuo, the residue taken up in DCM and extracted with water. The crude product obtained after evaporation of the solvent was purified by flash column chromatography on silica eluting with heptane/ethyl acetate giving the title compound as colorless oil (45 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598179B2
Source datasetuspto-grants-2013_12
ORD IDord-a13c9b70cec04809a99fb89fc9ce525c
Source noteuspto-grants-2013_12