Sodium Hydroxide → HCID 72188433, compound

HRID 881744Notes

Reaction equation

HRID 881744 reaction equation
[CH2:1]([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)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>>[CH2:1]([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)[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86700846HCID 86700846, compound

Product 1

HCID 72188433HCID 72188433, compound

Procedure

The title compound was prepared analogous to Example 4, Step 4 starting from methyl 2-(4-(4′-(5-isobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (56 mg, 0.12 mmol) and NaOH (0.35 ml, 0.35 mmol). After acidification with 1N HCl, the slurry was filtered and washed with water to afford the title compound as white solid after drying (52 mg, 97% yield). HR/MS (M+H)+ found 462.2399. calc. 462.2406. RT: 2.40 (Condition L). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.02-10.86 (m, 1H) 7.62 (s, 5H) 7.53-7.59 (m, 2H) 7.37 (d, J=8.59 Hz, 2H) 3.85 (s, 2H) 2.65 (d, J=7.07 Hz, 2H) 2.11-2.25 (m, 2H) 2.00-2.09 (m, 3H) 1.90-2.00 (m, 2H) 1.81 (d, J=13.39 Hz, 4H) 0.97 (d, J=6.82 Hz, 6H)

Workup

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

Sources & evidence

ORD record
ord-8fb4e57ddce34a6ba2a75c01ddf0899f
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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