Triacetoxyperiodinane → HCID 23648437, compound

HRID 1182314Notes

Reaction equation

HRID 1182314 reaction equation
[OH:1][C@@H:2]([CH2:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)(=[O:30])=[O:29])[C@@H:3]([NH:5][C:6](=[O:25])[O:7][C@H:8]([CH2:13][N:14]1[C:18]2[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:17]=2[N:16]=[CH:15]1)[C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:4].O[C@H](CNS(C1C=CC=CN=1)(=O)=O)[C@@H](NC(=O)O[C@H](CN1C2C=C(Cl)C(Cl)=CC=2N=C1)C(C)(C)C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH3:4][C@H:3]([NH:5][C:6](=[O:25])[O:7][C@H:8]([CH2:13][N:14]1[C:18]2[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:17]=2[N:16]=[CH:15]1)[C:9]([CH3:10])([CH3:12])[CH3:11])[C:2](=[O:1])[CH2:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)(=[O:29])=[O:30]

Participants

8

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58981705HCID 58981705, compoundHCID 58981757HCID 58981757, compound

Product 1

HCID 23648437HCID 23648437, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of 0.13 g (0.23 mmol) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S,2S)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S,2R)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate in 6 mL of chloroform was added 42 mg (0.1 mmol) of Dess-Martin periodinane, and the reaction mixture was stirred at room temperature for 1.25 h. The mixture was diluted with ethyl acetate and saturated aqueous sodium thiosulfate solution. The layers were mixed vigorously, and then a saturated aqueous sodium bicarbonate solution was added. The layers were separated, and the organic extract was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography eluting with a methanol:chloroform solution (1:9) to yield 64 mg (50%) of (1S)-1-[(5,6-dichloro-1H-benzimidazol-1-yl)methyl]-2,2-dimethylpropyl (1S)-1-methyl-2-oxo-3-[(2-pyridinylsulfonyl)amino]propylcarbamate ES-LCMS m/z 556 (M+H)+ retention time=3.66 min. HRMS C23H27Cl2N5O5S m/z 556.1188 (M+H)Cal; 556.1193 (M+H)Obs.

Workup

  1. additionThe layers were mixed vigorously
  2. customThe layers were separated
  3. extractionthe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a methanol

Sources & evidence

ORD record
ord-d2b733236336443188a0b32cfa2b9ef4
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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