HCID 19035377, compound → HCID 10763262, compound

HRID 263844Notes

Reaction equation

HRID 263844 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]2[S:20][C:19]3[S:21][C:22]([CH:24]=[O:25])=[CH:23][C:18]=3[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-:26]Cl=O.[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][C:16]2[S:20][C:19]3[S:21][C:22]([C:24]([OH:26])=[O:25])=[CH:23][C:18]=3[CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 19035377HCID 19035377, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 10763262HCID 10763262, compound

Procedure

5-3 (2.0 g, 5.27 mmol) was treated with NaClO2 (5.27 g, 58.3 mmol) with stirring at room temperature for 16 h. The reaction mixture was concentrated and partitioned between EtOAc (10 ml) and 3 ml of 1N NaHSO4. The organic phase was dried (MgSO4), concentrated and the solvent was removed. The residue was triturated with hexane to provide 5-4. as a white solid. 1H NMR (300 MHz, CD3OD) δ1.17 (2H, m), 1.46 (9H, s), 1.70 (4H, m), 2.68 (2H, t), 2.92 (2H, t), 4.10 (2H, bd), 6.95 (1H, s), 7.94 (1H, s).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between EtOAc (10 ml) and 3 ml of 1N NaHSO4
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customthe solvent was removed
  6. customThe residue was triturated with hexane
  7. customto provide 5-4

Sources & evidence

ORD record
ord-2d5f29c6f8f642798057601da6b8cadf
Source dataset
uspto-grants-1997_07
Patent number
US05646000

Reaction notes

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