Water → HCID 53682521, compound

HRID 326705Notes

Reaction equation

HRID 326705 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[CH2:5][C:6]1[C:7]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=C)=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[N:8][CH:9]=[N:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.[O-:38]I(=O)(=O)=O.[Na+].O>[Os](=O)(=O)(=O)=O.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[CH2:5][C:6]1[C:7]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=[O:38])=[CH:28][CH:27]=2)(=[O:24])=[O:25])=[N:8][CH:9]=[N:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1

Participants

6

Reactant 3

HCID 962WaterHCID 19735313HCID 19735313, compoundHCID 23667635Sodium periodate

Product 1

HCID 53682521HCID 53682521, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

318 mg of rac-N-[5-(o-methoxybenzyl)-6-[2-[(tetrahydro-2H-pyran-2-yl]oxy]ethoxy]-4-pyrimidinyl]-p-vinylbenzenesulfonamide, 5.3 mg of osmium tetroxide and 270 mg of sodium(meta)periodate were added in succession to a mixture of 1.5 ml of water and 4 ml of dioxane at room temperature. After stirring at room temperature for 1 hour, the dioxane was distilled under reduced pressure. Thereafter, the aqueous phase was extracted three times with ethyl acetate. The ethyl acetate was washed twice with water and once with NaCl solution (saturated), dried and distilled under reduced pressure. The residue was chromatographed over 30 g of SiO2 with CH2Cl2 /ethyl acetate and yielded 150 mg of rac-p-[[5-(o-methoxybenzyl)-6-[2-[(tetra-hydro-2H-pyran-2-yl)oxy]ethoxy]-4-pyrimidinyl]sulfamoyl]-benzaldehyde as white foam. MS: 527 (M); 443 ##STR12## (--OCH3 +SO2).

Workup

  1. distillationthe dioxane was distilled under reduced pressure
  2. extractionThereafter, the aqueous phase was extracted three times with ethyl acetate
  3. washThe ethyl acetate was washed twice with water and once with NaCl solution (saturated)
  4. customdried
  5. distillationdistilled under reduced pressure
  6. customThe residue was chromatographed over 30 g of SiO2 with CH2Cl2 /ethyl acetate

Sources & evidence

ORD record
ord-5123c56b9e4e435c95bd462e9ac0d25c
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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