Lithium Hydroxide → HCID 24957552, compound

HRID 1430617Notes

Reaction equation

HRID 1430617 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:27])[C:13]([CH3:26])([O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH3:14])[S:9][CH:10]=1)C.[Li+].[OH-]>C1COCC1.CO.O>[CH3:26][C:13]([O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)([CH3:14])[C:12]([NH:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:28])=[O:3])[N:7]=1)=[O:27]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86642357HCID 86642357, compound

Product 1

HCID 24957552HCID 24957552, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2-[2-Methyl-2-(naphthalen-1-yloxy)-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester (0.196 g, 5 mmol) in THF (2 ml) and MeOH (1 ml) added a solution of LiOH (0.021 g, 25 mmol) in H2O (1 ml) and stirred at r.t. for 18 h. Solvents were evaporated under reduced pressure and residue was dissolved in water (5 ml) and extracted with ether (2×2 ml). The aqueous phase was acidified with citric acid solution, extracted in EtOAc (2×30 ml), dried over Na2SO4 and the solvent was evaporated under reduced pressure to obtain {2-[2-Methyl-2-(naphthalen-1-yloxy)-propionylamino]-thiazol-4-yl}-acetic acid (0.16 g, 89%). 1H NMR (400 MHz, CDCl3): δ1.72 (s, 6H), 3.42 (s, 2H), 6.34 (s, 1H), 6.74 (d, J=7.2 Hz, 1H), 7.29 (d, J=8 Hz, 1H), 7.49-7.55 (m, 3H), 7.83-7.85 (m, 1H), 8.23-8.25 (m, 1H), MS (EI) m/z: 371.00 (M+1).

Workup

  1. customSolvents were evaporated under reduced pressure and residue
  2. dissolutionwas dissolved in water (5 ml)
  3. extractionextracted with ether (2×2 ml)
  4. extractionextracted in EtOAc (2×30 ml)
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-337229a6d32746f18b7372d95a42826b
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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