Triacetoxyperiodinane → HCID 24958964, compound

HRID 2381839Notes

Reaction equation

HRID 2381839 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:20]=[C:19]([CH:21]([OH:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:18]=[N:17]2)=[N:13][C:12]=1[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:21]([C:19]1[N:18]=[N:17][N:16]([C:14]2[S:15][C:11]([C:9]([NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[C:12]([CH3:29])[N:13]=2)[CH:20]=1)(=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 24958232HCID 24958232, compound

Product 1

HCID 24958964HCID 24958964, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-benzyl-2-(4-(hydroxy(phenyl)methyl)-1H-1,2,3-triazol-1-yl)-4-methylthiazole-5-carboxamide (0.18 g, 0.44 mmol) and Dess-Martin periodinane (0.28 g, 0.67 mmol) in dichloromethane (20 mL) was stirred at ambient temperature for 3 hours and washed with 10% aqueous solution of sodium thiosulfate (20 mL) and saturated aqueous sodium bicarbonate (20 mL). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid in 53% yield: mp 176-178° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.48 (s, 1H), 9.06 (t, J=6.0 Hz, 1H), 8.22 (d, J=6.0 Hz, 2H), 7.77-7.75 (m, 1H), 7.62 (t, J=6.0 Hz, 2H), 7.39-7.25 (m, 5H), 4.47 (d, J=6.0 Hz, 2H), 2.65 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 184.5, 160.0, 154.0, 152.6, 146.9, 138.9, 136.1, 133.7, 129.9, 128.7, 128.3, 127.3, 126.9, 126.8, 125.7, 42.8, 17.1; MS (ES+) m/z 404.3 (M+1).

Workup

  1. washwashed with 10% aqueous solution of sodium thiosulfate (20 mL) and saturated aqueous sodium bicarbonate (20 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-96e1aa3976f14edaaa5d83ebe7e2d19b
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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