Sodium Hydroxide → HCID 58961586, compound

HRID 916966Notes

Reaction equation

HRID 916966 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[C:11]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=2)[N:10]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([F:35])[CH:29]=2)[N:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58961593HCID 58961593, compound

Product 1

HCID 58961586HCID 58961586, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of the product from Example 104 Step F (0.280 g; 0.541 mmol) in methanol (4 mL) and THF (1 mL) in a round bottom flask was treated with 3N aq. NaOH (1.08 mL; 3.24 mmol) and heated to 50° C. for 2 hours. The volatiles were removed in vacuo, and the reaction was quenched with saturated aq. NaHSO4 solution and extracted with methylene chloride (5×). The combined extracts were dried (Na2SO4), filtered, and concentrated in vacuo to afford the crude product. NMR and LCMS indicated good purity and the crude product was used without further purification: m/e=504 (M+1).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe reaction was quenched with saturated aq. NaHSO4 solution
  3. extractionextracted with methylene chloride (5×)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b31c51f674b14747a06029b6b1bd1a96
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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