Water → HCID 131727784, compound

HRID 1438108Notes

Reaction equation

HRID 1438108 reaction equation
[CH:1]([S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:11]1[C@@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13][N:12]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:3])[CH3:2].[OH:27]OS([O-])=O.[K+].[OH2:33]>CO>[CH:1]([S:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:11]1[C@@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13][N:12]1[C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])(=[O:27])=[O:33])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 131727785HCID 131727785, compound

Product 1

HCID 131727784HCID 131727784, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 13A (0.24 g, 0.63 mmol) in methanol (3 mL) was added Oxone® (1.16 g, 1.90 mmol) in water (3 mL) at 0° C. The reaction was stirred for 3 h at rt. The reaction was quenched with 5% sodium bisulfite and then neutralized with 1 M sodium hydroxide. The solvent was evaporated and the aqueous layer was extracted with dichloromethane (3×). The organic extracts were combined, washed with saturated sodium chloride and dried over sodium sulfate. The solvent was evaporated and the crude residue was purified by flash column chromatography to give 0.17 g of 13B.

Workup

  1. customThe reaction was quenched with 5% sodium bisulfite
  2. customThe solvent was evaporated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×)
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-5a1a7b6ced1e4786a32a782c1992b3c0
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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