Water → HCID 68460621, compound

HRID 2197965Notes

Reaction equation

HRID 2197965 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[NH:18][C:19]2[C:28]3[C:23](=[N:24][C:25]([CH3:29])=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:5]=1.C1COCC1.O.[Li+].[OH-]>CC(O)=O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:30])=[O:2])=[C:12]([NH:18][C:19]2[C:28]3[C:23](=[N:24][C:25]([CH3:29])=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68460633HCID 68460633, compound

Product 1

HCID 68460621HCID 68460621, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

The product from Example 208c (447 mg, 1.065 mmol) was dissolved in 5 ml of a 1:1 (THF:water) solution. To this was added LiOH (51 mg, 2.129 mmol) and the reaction mixture was heated to 60° C. for 2 h the reaction mixture was then allowed to cool to room temperature and brought to neutral with HOAc. The product was extracted with ethyl acetate. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound (180 mg, 42%).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe product was extracted with ethyl acetate
  3. dry with materialDried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9b65d763420a488590ea1bc9b85e6954
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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