Hydrochloric Acid → HCID 69420594, compound

HRID 970215Notes

Reaction equation

HRID 970215 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:18]([C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[C:19]1[CH:24]=[CH:23][C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][CH:20]=1)[C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([F:17])[CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:39]O.Cl.O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:18]([C:34]([N:36]([CH3:37])[CH3:38])=[O:35])[C:19]1[CH:20]=[CH:21][C:22]([OH:39])=[CH:23][CH:24]=1)[C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([F:17])[CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 11678186HCID 11678186, compound

Product 1

HCID 69420594HCID 69420594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.0 g (7.50 mmol) of material from Step A above in 75 mL of tetrahydrofuran at 0° C. was added 1.25 mL of an aqueous solution of 30% hydrogen peroxide. After 1 h, the solution was allowed to warm up to ambient temperature and stirring continued for 2 h. The reaction mixture was acidified with 1N hydrochloric acid to pH 4. Additional water was added, and the aqueous layer was extracted with ethyl acetate (three times). The combined organic extracts were washed with saturated brine, dried (magnesium sulfate) and concentrated under reduced pressure. The resulting oil was purified by flash chromatography (silica gel, methanol/ethyl acetate) to afford the title compound. LC-MS 424.2 (M+1).

Workup

  1. waitcontinued for 2 h
  2. extractionthe aqueous layer was extracted with ethyl acetate (three times)
  3. washThe combined organic extracts were washed with saturated brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil was purified by flash chromatography (silica gel, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-1a858dd5150b4f08baf2365980dcabe6
Source dataset
uspto-grants-2007_12
Patent number
US07309714B2

Reaction notes

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