Sodium Hydroxide → HCID 89872226, compound

HRID 881730Notes

Reaction equation

HRID 881730 reaction equation
[CH:1]1([C:4]2[O:8][C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]56[CH2:29][CH2:28][C:25]([CH2:30][C:31]([O:33]C)=[O:32])([CH2:26][CH2:27]5)[O:24][CH2:23]6)=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+:36]>>[Na+:36].[CH:1]1([C:4]2[O:8][C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]56[CH2:29][CH2:28][C:25]([CH2:30][C:31]([O-:33])=[O:32])([CH2:26][CH2:27]5)[O:24][CH2:23]6)=[CH:18][CH:17]=4)=[CH:14][CH:15]=3)=[N:6][N:5]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 89872536HCID 89872536, compound

Product 1

HCID 89872226HCID 89872226, compound

Procedure

The title compound was prepared analogous to Example 4, Step 5 starting from methyl 2-(4-(4′-((5-cyclopropyl-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (413 mg, 0.90 mmol) and NaOH (2.70 ml, 2.70 mmol). After completion of the reaction, the mixture was concentrated to dryness and taken up in water. The resulting slurry was filtered and washed with water to afford the title compound as white solid after drying (392 mg, 93% yield). HR/MS (M+H)+ found 446.2077. calc. 446.2080. RT: 1.54 (Condition L). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.54 (br. s., 1H) 7.58-7.64 (m, 4H) 7.55 (d, J=8.34 Hz, 2H) 7.36 (d, J=8.34 Hz, 2H) 3.84 (s, 2H) 2.16-2.27 (m, 2H) 2.13 (tt, J=8.37, 5.02 Hz, 1H) 2.00 (s, 2H) 1.88-1.99 (m, 2H) 1.69-1.88 (m, 4H) 1.03-1.10 (m, 2H) 0.91-0.98 (m, 2H)

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated to dryness
  3. filtrationThe resulting slurry was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-e0b2f09b40524b7d9baaf909e910c077
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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