Lithium hydroxide, monohydrate → 3-[(3-Methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acid

HRID 548734Notes

Reaction equation

HRID 548734 reaction equation
O.[OH-].[Li+].[CH3:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][C:14]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@H:28]4[CH2:32][CH2:31][O:30][CH2:29]4)[CH:26]=3)[C:20]([O:22]C)=[O:21])=[CH:15][C:8]=2[O:7][CH2:6]1>O.C1COCC1>[CH3:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][C:14]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@H:28]4[CH2:32][CH2:31][O:30][CH2:29]4)[CH:26]=3)[C:20]([OH:22])=[O:21])=[CH:15][C:8]=2[O:7][CH2:6]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57663180methyl 3-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate

Product 1

HCID 576631863-[(3-Methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoic acidYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (13 mg, 0.3 mmol) in water (2.5 mL) was added to a solution of methyl 3-[(3-methyl-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzoate (0.12 g, 0.3 mmol) in THF (5 mL) and stirred at RT for 20 hours. The THF was removed in vacuo and the aqueous layer was washed with ethyl acetate (50 mL) to remove any impurities. The aqueous layer was acidified and extracted into ethyl acetate (2×50 mL), washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo to give the desired compound as a white solid (110 mg).

Workup

  1. customThe THF was removed in vacuo
  2. washthe aqueous layer was washed with ethyl acetate (50 mL)
  3. customto remove any impurities
  4. extractionextracted into ethyl acetate (2×50 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-48bb7e981e74423fab58e65937850657
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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