Hydrochloric Acid → HCID 23506742, compound

HRID 1883537Notes

Reaction equation

HRID 1883537 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:8]=[C:9]([CH2:27][N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[C:10]=1[N:11]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]#[C:25][CH3:26])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:12])=[O:4].[OH-].[Na+].Cl>C1COCC1.CO>[CH2:23]([O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([N:11]([CH3:12])[C:10]2[C:9]([CH2:27][N:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)=[CH:8][C:7]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])(=[O:15])=[O:14])=[CH:21][CH:20]=1)[C:24]#[C:25][CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69904168HCID 69904168, compound

Product 1

HCID 23506742HCID 23506742, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.965 g (1.72 mmol) of the product of Example 74 and 8.6 mL (8.59 mmol) of 1N NaOH in 8.6 mL of THF and 8.6 mL of methanol was heated to reflux for 18 h. The reaction mixture was cooled and neutralized with 3N HCl. The organic solvents were removed and the resulting aqueous solution was extracted with dichloromethane. The organic layer was separated, washed with water and brine, dried over Na2CO3 and concentrated in vacuo. The residue was triturated with ether to provide 0.829 g (89%) of the desired product as a cream solid. Electrospray Mass Spec 548.1 (M+H)+

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. customThe organic solvents were removed
  5. extractionthe resulting aqueous solution was extracted with dichloromethane
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over Na2CO3
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-64b69740616344e08db0a4488b625b7e
Source dataset
uspto-grants-2004_07
Patent number
US06762178B2

Reaction notes

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