Acetic Acid → HCID 66880527, compound

HRID 1893589Notes

Reaction equation

HRID 1893589 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][N:8]([C:23]1[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[CH:26]=[CH:25][C:24]=1[CH3:32])[CH2:9][C:10]([N:12]([N:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1)[CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.Cl.NO.[OH-].[Na+].CO[CH:45](OC)[N:46](C)C>>[C:1]([O:5][C:6](=[O:33])[CH2:7][N:8]([CH2:9][C:10]([N:12]([N:14]1[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22]1)[CH3:13])=[O:11])[C:23]1[CH:28]=[C:27]([C:29]2[O:30][N:46]=[CH:45][N:31]=2)[CH:26]=[CH:25][C:24]=1[CH3:32])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 78373Dimethylformamide dimethyl acetalHCID 443297Hydroxyamine hydrochlorideHCID 66882053HCID 66882053, compound

Product 1

HCID 66880527HCID 66880527, compoundYield 52%

Conditions

Temperature
110 °C

Procedure

The compound (400 mg, 0.88 mmol) of Example 81, step B, was dissolved in N,N-dimethylformamide dimethylacetal (2.5 ml), and the mixture was stirred at 110° C. for 1 hr. The reaction mixture was concentrated and the obtained residue was dissolved in 1,4-dioxane (1.5 ml). Then, acetic acid (1.5 ml), hydroxylamine hydrochloride (95 mg, 1.33 mmol) and 2N aqueous sodium hydroxide solution (0.7 ml, 1.4 mmol) were added, and the mixture was stirred at 90° C. for 30 min. The reaction mixture was concentrated under reduced pressure, diluted with water, and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-dichloromethane) to give the title compound (219 mg, yield 52%) as a pale-yellow amorphous solid

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe obtained residue was dissolved in 1,4-dioxane (1.5 ml)
  3. stirringthe mixture was stirred at 90° C. for 30 min
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additiondiluted with water
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationthe insoluble material was filtered off
  9. concentrationthe solution was concentrated under reduced pressure
  10. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-9f5ae5447a404f29bb77338cb102a398
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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