Potassium bisulfate → HCID 58859168, compound

HRID 1349502Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[CH:11]=[C:12]([CH:24]=[O:25])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].[CH2:35]([Mg]Br)[CH3:36].S([O-])(O)(=O)=O.[K+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]([CH2:26][CH:27]([O:28][CH3:29])[O:30][CH3:31])[CH:11]=[C:12]([CH:24]([OH:25])[CH2:35][CH3:36])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-formyl-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (168 mg) in tetrahydrofuran (6 ml) was added dropwise 0.89 M ethylmagnesium bromide (1.09 ml) with stirring at −78° C. After stirring at the same temperature for 10 min, 5% aqueous potassium hydrogen sulfate solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried and concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1–4:1) to give 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-(1-hydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (137 mg).

Workup

stirringAfter stirring at the same temperature for 10 min
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
customdried
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1–4:1)

Sources & evidence

ORD record: ord-8ffdbefe3df249c0a6604fc816c170cc
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211572B2

Reaction notes

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