Water → HCID 178464135, compound

HRID 1170429Notes

Reaction equation

HRID 1170429 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:35])[C:17]2[C:12](=[CH:13][C:14]([C:22]#[N:23])=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:24][C@H:25]2[CH2:28][C@H:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:26]2)[C:10]1=[O:34].[OH-].[K+].C(OCC)(=[O:40])C.O>C(O)(C)(C)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:35])[C:17]2[C:12](=[CH:13][C:14]([C:22]([NH2:23])=[O:40])=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:24][C@H:25]2[CH2:28][C@H:27]([N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])[CH2:26]2)[C:10]1=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 178464134HCID 178464134, compound

Product 1

HCID 178464135HCID 178464135, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound of Example 1-3 (1.76 g, 3.34 mmol) in tert-butyl alcohol (34 mL) was added potassium hydroxide (1.76 g, 31.4 mmol), and the mixture was stirred at 50° C. for 1.5 hours. To the reaction solution were added ethyl acetate (100 mL) and water (2 mL), and then the mixture was dried over magnesium sulfate and filtered. The mixture was evaporated, and then dissolved in ethyl acetate again and filtered. The filtrate was evaporated, and then thereto were added tetrahydrofuran (100 mL) and 1M hydrochloric acid (5 mL), and the mixture was evaporated, and then the residual water was removed by azeotropic distillation with toluene. The resulting solid was washed with diethyl ether, and then dried to give the titled compound (1.89 g, 97%).

Workup

  1. dry with materialthe mixture was dried over magnesium sulfate
  2. filtrationfiltered
  3. customThe mixture was evaporated
  4. dissolutiondissolved in ethyl acetate again
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. additionwere added tetrahydrofuran (100 mL) and 1M hydrochloric acid (5 mL)
  8. customthe mixture was evaporated
  9. customthe residual water was removed by azeotropic distillation with toluene
  10. washThe resulting solid was washed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-7172a814487645148a60b7912bbf4735
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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