Sodium Hydroxide → HCID 86700874, compound

HRID 881769Notes

Reaction equation

HRID 881769 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[O:29][C:26]([CH2:30][C:31]([O:33]C)=[O:32])([CH2:27][CH2:28]4)[CH2:25][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+]>C1COCC1.CO>[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[O:29][C:26]([CH2:30][C:31]([OH:33])=[O:32])([CH2:27][CH2:28]4)[CH2:25][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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86700875HCID 86700875, compound

Product 1

HCID 86700874HCID 86700874, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-(4′-((5-(tert-butyl)-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-7-oxabicyclo[2.2.1]heptan-1-yl)acetate (110 mg, 0.24 mmol) in THF (4 mL) and Methanol (1 mL) was added 1N NaOH (0.72 mL, 0.72 mmol) and the reaction was let stir at rt for 2 hr. The resulting yellow reaction mixture was partially concentrated by rotary evaporation in vacuo (rt water bath). The yellow solution was diluted with MeOH, filtered and purified on preparative HPLC (10-50% MeCN:5 mM NH4OH) to afford 52 mg (49%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.36 (s, 9H), 1.63-1.82 (m, 4H), 1.90-2.02 (m, 2H), 2.08-2.21 (m, 2H), 2.79 (s, 2H), 7.42 (d, J=8.3 Hz, 2H), 7.56-7.70 (m, 6H), 10.51 (br. s., 1H). ESI-MS m/z: 448.1 [M+H]+, retention time 1.08 min (condition E). HR/MS [M+H]+: found 448.2236. calc. 448.2218. RT: 2.27 (Condition L).

Workup

  1. concentrationThe resulting yellow reaction mixture was partially concentrated by rotary evaporation in vacuo (rt water bath)
  2. additionThe yellow solution was diluted with MeOH
  3. filtrationfiltered
  4. custompurified on preparative HPLC (10-50% MeCN:5 mM NH4OH)

Sources & evidence

ORD record
ord-4497d9c679a44d158793769bbf1568af
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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