Hydrochloric Acid → HCID 67406407, compound

HRID 1174381Notes

Reaction equation

HRID 1174381 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:25]([OH:27])=[O:26])[C:20](SC)([CH3:22])[CH3:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:28](=O)(O)[O-].[Na+].[OH-].[Na+].O[O:36][S:37]([O-:39])=O.[K+].Cl>O.C(OCC)(=O)C.CC(C)=O>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:25]([OH:27])=[O:26])[C:20]([S:37]([CH3:28])(=[O:39])=[O:36])([CH3:22])[CH3:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 67408509HCID 67408509, compound

Product 1

HCID 67406407HCID 67406407, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Example 156A (2.13 g) in mixture of water (11 mL) and acetone (5.5 mL) at room temperature were added sodium bicarbonate (3.7 g, 44.0 mmol) and sodium hydroxide solution (6.6 mL, 1 N). To this mixture was added a solution of oxone in water (4.75 g in 15 mL) dropwise at room temperature and the reaction was stirred for 2 hours. Ethyl acetate was added and the solution was adjusted to pH 3 with concentrated HCl. The organic was washed with brine and dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with a gradient starting with dichloromethane and ending with 20% methanol in dichloromethane to give the product (0.70 g, 42% over 2 steps).

Workup

  1. washThe organic was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with a gradient
  6. customto give the product (0.70 g, 42% over 2 steps)

Sources & evidence

ORD record
ord-57eded82b9e541b0bfd26272367fce8c
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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