Hydrogen Peroxide → 4-(2-((tert-Butoxycarbonyl)amino)pyridin-4-yl)benzoic acid

HRID 1459426Notes

Reaction equation

HRID 1459426 reaction equation
[CH3:1][C:2]([CH3:22])([O:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)=[O:6])[CH3:3].[OH:23]S([O-])(=O)=O.[K+].OO.[O-]Cl=O.[Na+]>CC#N.O.CCOC(C)=O>[CH3:3][C:2]([CH3:22])([O:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:23])=[O:19])=[CH:20][CH:21]=2)[CH:11]=[CH:10][N:9]=1)=[O:6])[CH3:1]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 516920Potassium bisulfateHCID 21912851Carbamic acid, (4-(4-formylphenyl)-2-pyridinyl)-, 1,1-dimethylethyl esterHCID 23668197Sodium Chlorite

Product 1

HCID 227099344-(2-((tert-Butoxycarbonyl)amino)pyridin-4-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

17-4 (1.0 g, 3.4 mmol) is slurried in CH3CN (40 mL). 10% KHSO4 (1.3 mL) and 30% H2O2 (0.957 mL) are added and the solution is cooled in an ice bath. NaClO2 (8.5 mmol, 770 mg) is added dropwise in 50 mL water over 20 min. The reaction is stirred for 16 hrs. The reaction mixture is diluted w/EtOAc and washed with saturated NaHCO3 (2×). The aqueous layers are combined, acidifed with 10% KHSO4, and extracted w/CH2Cl2 (2×) and EtOAc (2×) to give 17-5 as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.6-12.8 (bs, 1H), 9.9 (s, 1H), 8.3 (d, 1H), 8.0-8.1 (m, 3H), 7.9 (d, 2H), 7.3 (d, 1H), 1.5 (s, 9H). ##STR88## Ethyl 2-(4-(4-(2-(1,1-Dimethylethoxycarbonylamino)pyrid-4-yl)carbonylamino)phenoxy)acetate (17-6)

Workup

  1. temperaturethe solution is cooled in an ice bath
  2. washwashed with saturated NaHCO3 (2×)
  3. extractionextracted w/CH2Cl2 (2×) and EtOAc (2×)

Sources & evidence

ORD record
ord-2a7ca3646bcc4de2b22460c737c7db35
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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