Hydrochloric Acid → HCID 22262699, compound

HRID 1455840Notes

Reaction equation

HRID 1455840 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:35])[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11]([NH:16][C:17]([C:19]1[C:20]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:18])=[CH:10][CH:9]=2)=[O:5])C.[Li+].[OH-].Cl>C1COCC1.CO.O>[Cl:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:16][C:17]([C:19]3[C:20]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=4)=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:18])[CH:12]=2)[N:7]([CH3:35])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68954487HCID 68954487, compound

Product 1

HCID 22262699HCID 22262699, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of step (d) may be hydrolyzed as follows: the compound (5.51 g) was dissolved in THF (120 mL) and methanol (40 mL). Under stirring conditions was added LiOH (1.32 g) in water (40 mL). The reaction mixture was stirred at room temperature overnight. To the reaction mixture was then added 1 N HCl solution (60 mL), and the aqueous layer was extracted with EtOAc (250 mL). The organic layer was washed with brine (200 mL), and dried (MgSO4). The solvent was evaporated in vacuo to give the crude product which was purified by recrystallization from 1:1 EtOAc/ether to afford 4.4 g of the title compound.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (250 mL)
  2. washThe organic layer was washed with brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated in vacuo
  5. customto give the crude product which
  6. customwas purified by recrystallization from 1:1 EtOAc/ether

Sources & evidence

ORD record
ord-74572e06822e4319a723971c8e196d89
Source dataset
uspto-grants-2009_01
Patent number
US07482368B2

Reaction notes

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