Lithium Hydroxide → HCID 68956958, compound

HRID 1888369Notes

Reaction equation

HRID 1888369 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:31])[C:6]1[CH:11]=[C:10]([NH:12][C:13](=[O:28])[C@:14]([OH:27])([CH3:26])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([F:25])[CH:18]=2)[CH:9]=[CH:8][C:7]=1[C:29]#[N:30]>C1COCC1.CO>[C:29]([C:7]1[CH:8]=[CH:9][C:10]([NH:12][C:13](=[O:28])[C@:14]([OH:27])([CH3:26])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([F:25])[CH:18]=2)=[CH:11][C:6]=1[C:5]([OH:31])=[O:4])#[N:30]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68957633HCID 68957633, compound

Product 1

HCID 68956958HCID 68956958, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 M LiOH (34 ml) was added to a solution of 2-cyano-5-[(S)-3-(4-cyano-3-fluorophenoxy)-2-hydroxy-2-methylpropionylamino]benzoic acid methyl ester (4.52 g, 11.4 mmol) in THF (50 ml) and methanol (6 ml) at 16-18° C. The resulting solution was stirred at room temperature for 2.5 h. The solvents were evaporated and pH was adjusted to 2 with HCl solution. The product was extracted into ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (eluent: CH2Cl2/MeOH 98:2). Trituration in hot CH2Cl2, cooling to room temperature and filtration yielded the title compound.

Workup

  1. customThe solvents were evaporated
  2. extractionThe product was extracted into ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography (eluent: CH2Cl2/MeOH 98:2)
  7. temperatureTrituration in hot CH2Cl2, cooling to room temperature
  8. filtrationfiltration

Sources & evidence

ORD record
ord-6698e76b11644626aedb4815b547c347
Source dataset
uspto-grants-2013_08
Patent number
US08501814B2

Reaction notes

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