Lithium Hydroxide → HCID 59404865, compound

HRID 1929784Notes

Reaction equation

HRID 1929784 reaction equation
[Cl:1][C:2]1[C:3]([F:37])=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:35][CH3:36])=[C:17]([O:20][CH:21]4[CH2:26][CH2:25][N:24]([C:27](=[O:34])/[CH:28]=[CH:29]\[C:30]([O:32]C)=[O:31])[CH2:23][CH2:22]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[C:3]([F:37])=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:35][CH3:36])=[C:17]([O:20][CH:21]4[CH2:22][CH2:23][N:24]([C:27](=[O:34])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31])[CH2:25][CH2:26]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59404866HCID 59404866, compound

Product 1

HCID 59404865HCID 59404865, compoundYield 121.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.1 g of the compound obtained in Example 83 was diluted in 2 ml of tetrahydrofuran, and 0.1 ml of a 3M lithium hydroxide solution was added thereto at 0° C. The resulting mixture was stirred at room temperature for two hours and extracted with chloroform. The aqueous layer was acidified with a 1N HCl and extracted three times with chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was purified by column chromatography (methylene chloride:methanol=5:1) to obtain the title compound (118 mg, 48%).

Workup

  1. customat 0° C
  2. extractionextracted with chloroform
  3. extractionextracted three times with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under a reduced pressure
  7. customThe resulting residue was purified by column chromatography (methylene chloride:methanol=5:1)

Sources & evidence

ORD record
ord-1dbf10e19b24495bb5d7f759408adaf3
Source dataset
uspto-grants-2012_05
Patent number
US08188102B2

Reaction notes

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