HCID 11486489, compound → HCID 11429637, compound

HRID 1272581Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6](=[O:29])/[CH:7]=[CH:8]/[C:9]1[C:10]([CH:26]2[CH2:28][CH2:27]2)=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:2]>CC(O)C>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH:6]([OH:29])/[CH:7]=[CH:8]/[C:9]1[C:10]([CH:26]2[CH2:28][CH2:27]2)=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:2]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of (E)-5-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-oxo-pent-4-enoic-acid-ethylester (105.8 mg, 0.262 mmol) and Ru[(1R,2R)-p-TsNCH(C6H5)CH(C6H5)NH](η6-p-cymene) (6.2 mg, 0.104 mmol) in 2-propanol (2.6 ml) is stirred at 23° C. for 72 h. The reaction mixture is concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel using a 4:1 hexane-MTBE (methyl-tert-butyl-ether) mixture as eluent to afford of (E)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic-acid-ethylester.

Workup

concentrationThe reaction mixture is concentrated under reduced pressure
customThe residue is purified by flash chromatography on silica gel using a 4:1 hexane-MTBE (methyl-tert-butyl-ether) mixture as eluent

Sources & evidence

ORD record: ord-533d2740a1f04c8d93aa681ccb276881
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208623B2

Reaction notes

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