Water → HCID 59625636, compound

HRID 2192811Notes

Reaction equation

C([O:4][CH2:5][CH:6]1[CH2:11][CH:10]([N:12]([C:17]([C:19]2[C:20]([NH:29][CH2:30][C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)=[N:21][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[N:23][CH:24]=2)=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][N:8]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:7]1)(=O)C.O.[OH-].[Na+]>CO>[C:25]([C:22]1[N:21]=[C:20]([NH:29][CH2:30][C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)[C:19]([C:17]([N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:10]2[CH2:11][CH:6]([CH2:5][OH:4])[CH2:7][N:8]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:9]2)=[O:18])=[CH:24][N:23]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of tert-butyl 3-[(acetyloxy)methyl]-5-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate (780 mg) in methanol (10 ml)-water (9 ml) was added 8 M aqueous sodium hydroxide solution (0.83 ml), and the mixture was stirred at 70° C. for 7 hr and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (5:95-100:0) was concentrated under reduced pressure to give the object compound (709 mg).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
washthe fraction eluted with ethyl acetate-hexane (5:95-100:0)
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-9a1363dc62074ebe8efc00fc45839e6e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329691B2

Reaction notes

Loading…