Lithium Hydroxide → HCID 178448326, compound

HRID 75765Notes

Reaction equation

HRID 75765 reaction equation
C[O:2][C:3](=[O:34])[C@@H:4]([NH:8][C:9]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[S:25][C:26]4[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=4[N:28]=3)=[CH:19][CH:18]=2)[CH:13]=1)=[N:10][OH:11])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-]>C1COCC1>[F:33][C:31]1[CH:30]=[CH:29][C:27]2[N:28]=[C:24]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([C:14]4[CH:13]=[C:12]([C:9]([NH:8][C@@H:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:34])=[O:2])=[N:10][OH:11])[O:16][N:15]=4)=[CH:18][CH:19]=3)[S:25][C:26]=2[CH:32]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178501506HCID 178501506, compound

Product 1

HCID 178448326HCID 178448326, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
42.5 °C

Procedure

To a solution of (S)-2-({3-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-N-hydroxy-isoxazole-5-carboximidoyl}-amino)-3-methyl-butyric acid methyl ester (0.3 g; 0.62 mmol) in THF (3 ml) was added 1N LiOH (0.81 ml; 0.81 mmol) under stirring for 48 hours, followed by heating at 40-45° C. for 2 hours. Solvent was removed from the reaction mixture and the residue was diluted with water (5 ml) and acidified to pH 2 with 2N HCl. The semisolid material obtained was extracted with EtOAc, washed with water (2×5 ml), and dried over anhydrous Na2SO4. The residue was purified by flash chromatography with 10-50% MeOH in chloroform. The pure material obtained was triturated with acetone and light petroleum, filtered and dried under vacuum pump to yield 0.16 g (55%) of the title compound. Mass

Workup

  1. customSolvent was removed from the reaction mixture
  2. additionthe residue was diluted with water (5 ml)
  3. customThe semisolid material obtained
  4. extractionwas extracted with EtOAc
  5. washwashed with water (2×5 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe residue was purified by flash chromatography with 10-50% MeOH in chloroform
  8. customThe pure material obtained
  9. customwas triturated with acetone and light petroleum
  10. filtrationfiltered
  11. customdried under vacuum pump

Sources & evidence

ORD record
ord-f7b2cec7d6e24777b04dd556fd35b9ef
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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