Hydrochloric Acid → HCID 69420594, compound

HRID 2242650Notes

Reaction equation

HRID 2242650 reaction equation
[CH3:1][N:2]([CH3:38])[C:3](=[O:37])[C@@H:4]([C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=1)[C@H:5]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([F:13])[CH2:9]1)=[O:7].[OH:39]O.[OH-].[Na+].Cl>C1COCC1.O>[C:17]([O:16][C:15](=[O:21])[NH:14][C@H:5]([C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([F:13])[CH2:9]1)=[O:7])[C@H:4]([C:22]1[CH:27]=[CH:26][C:25]([OH:39])=[CH:24][CH:23]=1)[C:3]([N:2]([CH3:1])[CH3:38])=[O:37])([CH3:19])([CH3:18])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 11678186HCID 11678186, compound

Product 1

HCID 69420594HCID 69420594, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the material from Step A (0.5 g, 0.94 mmol) in THF (10 mL) at 0° C. was added sequentially 30% hydrogen peroxide (0.16 mL, 1.4 mmol) and 3N aqueous sodium hydroxide (0.31 g, 0.94 mmol). After 1.5 h at this temperature, the mixture was allowed to warm to ambient temperature, and then water (50 mL) was added, and the resulting solution was adjusted to pH 5 by the addition of 1N hydrochloric acid. The mixture was extracted with ethyl acetate, and the combined extracts were washed with 10% aqueous sodium thiosulfate until the organic phase showed a negative peroxide test. The combined organics were washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purified by silica gel chromatography (0-10% methanol in ethyl acetate) to give the title compound as a white foam. LC/MS 424.3 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined extracts were washed with 10% aqueous sodium thiosulfate until the organic phase
  3. washThe combined organics were washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (0-10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-3e670853676e4cdb90ce51a97d4109b4
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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