Hydrochloric Acid → HCID 71293493, compound

HRID 2362305Notes

Reaction equation

HRID 2362305 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:27])[N:20]([CH2:22][C:23]([O:25]C)=[O:24])[N:21]=[C:8]2[N:7]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:6]=1[CH3:38])=[O:4].CO.[OH-].[Li+].Cl>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:27])[N:20]([CH2:22][C:23]([OH:25])=[O:24])[N:21]=[C:8]2[N:7]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:36])([F:35])[F:37])[CH:29]=2)[C:6]=1[CH3:38])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 71293480HCID 71293480, compound

Product 1

HCID 71293493HCID 71293493, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 25 (240 mg, 0.46 mmol) in THF (3 mL), was added MeOH (3 mL) followed by lithium hydroxide (3M in water, 200 μL, 0.6 mmol). The reaction mixture was stirred at RT for 2 hours, and then the volatiles were removed in vacuo. The resultant residue was dissolved in water, and the solution thus obtained was made acidic by addition of 6 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo to yield the title compound as a colourless oil (250 mg).

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionThe resultant residue was dissolved in water
  3. customthe solution thus obtained
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0d42b1a743d343749b16f99b8d731cd8
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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