Lithium Hydroxide → 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoic acid

HRID 2190170Notes

Reaction equation

[CH:1]1([C:4]2[CH:5]=[C:6]3[C:25]([C:26](=[O:29])[NH:27][CH3:28])=[C:24]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)[O:23][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.[Li+].[OH-:38].[NH4+].[Cl-]>CO.C1COCC1.O>[NH4+:8].[OH-:12].[CH3:6][C:7]#[N:8].[OH2:38].[CH:1]1([C:4]2[CH:5]=[C:6]3[C:25]([C:26](=[O:29])[NH:27][CH3:28])=[C:24]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)[O:23][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 23 °C

Procedure

Methyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate (17 mg, 0.033 mmol) was dissolved in MeOH/THF/H2O (2.33 mL, 3:1:3) and LiOH (0.13 mL, 0.13 mmol, 1M solution) was added and the mixture stirred at 23° C. overnight. The reaction was then neutralized by addition of NH4Cl and the aqueous extracted with EtOAc (3×10 mL) then washed with brine and dried over Na2SO4 and evaporated to dryness. HPLC (Basic method/NH4OH/CH3CN/H2O) yielded 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoic acid (5 mg, 0.01 mmol, 30%).

Workup

extractionthe aqueous extracted with EtOAc (3×10 mL)
washthen washed with brine
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-2be83a186049462da5ea2198136f9bce
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

Loading…