Sodium Hydroxide → HCID 86700881, compound

HRID 881775Notes

Reaction equation

HRID 881775 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][CH2:31][C:32]([O:34]C)=[O:33])([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][CH2:31][C:32]([OH:34])=[O:33])([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 86700880HCID 86700880, compound

Product 1

HCID 86700881HCID 86700881, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(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)propanoate (100 mg, 0.21 mmol) in THF (3.4 mL) and methanol (0.85 mL) was added 1N NaOH solution (0.63 mL, 0.63 mmol) and the reaction was let stir at rt for 2 h. The resulting yellow reaction mixture was partially concentrated by rotary revaporation (rt water bath) to remove THF. The resulting yellow mixture was diluted with methanol, filtered and purified on preparative HPLC (10-50% acetonitrile:5 mM NH4OH) and lyophilized to afford 83 mg (86%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.36 (s, 9H), 1.56-1.82 (m, 6H), 2.01-2.10 (m, 2H), 2.10-2.19 (m, 2H), 2.30-2.39 (m, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.60 (d, J=8.6 Hz, 2H), 7.62-7.67 (m, 4H) 10.51 (br. s., 1H). 13C NMR (100 MHz, DMSO-d6): δ ppm 174.5, 165.9, 159.5, 141.7, 138.3, 138.2, 133.1, 127.1, 125.8, 125.4, 117.1, 86.1, 85.5, 37.9, 34.9, 31.7, 30.2, 30.1, 27.8. ESI-MS m/z: 462.1 [M+H]+, retention time 1.13 min (condition E). HR/MS [M+H]+: found 462.2371. calc. 462.2393. RT: 1.96 (Condition L).

Workup

  1. concentrationThe resulting yellow reaction mixture was partially concentrated by rotary revaporation (rt water bath)
  2. customto remove THF
  3. additionThe resulting yellow mixture was diluted with methanol
  4. filtrationfiltered
  5. custompurified on preparative HPLC (10-50% acetonitrile:5 mM NH4OH)

Sources & evidence

ORD record
ord-bf265115f7a1485b9b9a087f2e72a151
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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