Potassium bisulfate → HCID 17917748, compound

HRID 1937812Notes

Reaction equation

CON(C)[C:4]([CH:6]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:13])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+]>C1COCC1.O>[CH:4]([CH:6]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:13])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

The amide from above (4.7 g, 14.7 mmol) was dissolved in 50 mL THF and added to a slurry of LiAlH4 (558 mg, 14.7 mmol) in 50 mL THF at −78° C. The reaction mixture was allowed to warm to 0° C. and maintained for 15 min, after which time it was cooled to −78° C. and cannulated into an ice-cooled solution of KHSO4 (8.16 g, 60 mmol) in 200 mL H2O. The resulting mixture was extracted with 5×100 mL EtOAc. The combined extracts were washed with 2×100 mL satd.NaHCO3 and 1×100 mL brine, dried with Na2SO4 and evaporated to an oily residue which was flash chromatographed through SiO2 (25% EtOAc/hexane—35% EtOAc/hexane) yielding 2.8 g (86%) of pyridine-2-carboxylic acid (1-formyl-3-methylbutyl)amide as a colorless oil which solidified on standing.

Workup

temperaturemaintained for 15 min
temperatureafter which time it was cooled to −78° C.
extractionThe resulting mixture was extracted with 5×100 mL EtOAc
washThe combined extracts were washed with 2×100 mL
dry with materialNaHCO3 and 1×100 mL brine, dried with Na2SO4
customevaporated to an oily residue which
customchromatographed through SiO2 (25% EtOAc/hexane—35% EtOAc/hexane)

Sources & evidence

ORD record: ord-75c309ff483c4009aeec41de1b034b52
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06395897B1

Reaction notes

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