Sodium Hydroxide → HCID 72188425, compound

HRID 881729Notes

Reaction equation

HRID 881729 reaction equation
[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34]C)=[O:33])([CH2:27][CH2:28]4)[O:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>>[C:1]([C:5]1[O:9][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[CH2:28][CH2:27][C:26]([CH2:31][C:32]([OH:34])=[O:33])([CH2:29][CH2:30]4)[O:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86700835HCID 86700835, compound

Product 1

HCID 72188425HCID 72188425, compound

Procedure

The title compound was prepared analogous to Example 4, Step 4 starting from methyl 2-(4-(4′-(5-tert-butyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (82 mg, 0.17 mmol) and NaOH (0.52 ml, 0.52 mmol). After acidification with 1N HCl, the slurry was filtered and washed with water to afford the title compound as white solid after drying (75 mg, 95% yield). HR/MS (M+H)+ found 462.2396. calc. 462.2392. RT: 2.75 (Condition L). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.07 (s, 1H) 10.51 (s, 1H) 7.62 (s, 4H) 7.58 (d, J=8.34 Hz, 2H) 7.38 (d, J=8.59 Hz, 2H) 3.90 (s, 2H) 2.33 (s, 2H) 1.82-2.07 (m, 8H) 1.36 (s, 9H)

Workup

  1. filtrationAfter acidification with 1N HCl, the slurry was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-607024f2e7784ec6a2810bf7f0b3df15
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

Loading…