Lithium hydroxide, monohydrate → HCID 118114356, compound

HRID 2284859Notes

Reaction equation

HRID 2284859 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[O:13][CH2:14][C:15]1[O:16][CH:17]=[C:18]([C:20]([O:22]C)=[O:21])[N:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.CO.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[O:13][CH2:14][C:15]1[O:16][CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118114363HCID 118114363, compound

Product 1

HCID 118114356HCID 118114356, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-[[3-[(S)-(tert-butoxycarbonylamino)-phenyl-methyl]phenoxy]methyl]oxazole-4-carboxylate (0.8 g, 1.825 mmol) in THF (9.2 mL) and methanol (9.2 mL) was added a solution of lithium hydroxide monohydrate (153.1 mg, 3.65 mmol) in water (3.6 mL). The reaction was stirred at room temperature for 18 h. The majority of the solvent was removed in vacuo. The residue was diluted with water (50 mL) and cooled to 0° C. 2N aqueous HCl (1.82 mL) was added dropwise. The reaction mixture was extracted with ethyl acetate (3×20 mL) and the combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a colourless solid (736 mg, 95%).

Workup

  1. customThe majority of the solvent was removed in vacuo
  2. additionThe residue was diluted with water (50 mL)
  3. temperaturecooled to 0° C
  4. addition2N aqueous HCl (1.82 mL) was added dropwise
  5. extractionThe reaction mixture was extracted with ethyl acetate (3×20 mL)
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdb223ed0ee1404bb9218ef15f2a8b84
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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