Acetic Acid → HCID 178452602, compound

HRID 1509121Notes

Reaction equation

HRID 1509121 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][C:21]([C:30]#[N:31])=[C:20]([OH:32])[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].OO.C(O)(=[O:40])C>C(O)C.O>[C:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][C:21]([C:30](=[O:40])[NH2:31])=[C:20]([OH:32])[N:19]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178452601HCID 178452601, compound

Product 1

HCID 178452602HCID 178452602, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of tert-butyl(1-(4-(5-cyano-6-hydroxy-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate (14.6 g, 3.58 g, 0.033 mol) in ethanol (112 ml) and water (112 ml) at room temperature was added sodium hydroxide solution (6M, 54.4 ml) and hydrogenperoxide (30%, 21.9 ml). The resulting mixture was heated at 50° C. for 16 h. After cooled down to 0° C., the mixture was added acetic acid to adjust pH=4. The resulting precipitate was filtered and the filter cake was dried to give the title compound as white solid (10.8 g, 72%). LCMS (Method A): RT=5.88 min, M+1=460. 1H NMR (500 MHz, DMSO-d6): 9.65 (1H, br), 8.10 (1H, s), 7.25-7.05 (7H, m), 6.98 (2H, m), 2.45-2.25 (4H, m), 2.0-1.95 (1H, m), 1.79-1.75 (1H, m), 1.3-1.0 (91-1, br).

Workup

  1. temperatureAfter cooled down to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. customthe filter cake was dried

Sources & evidence

ORD record
ord-b9c5577f32dd42caa0d81c8e92fc735b
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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