Lithium hydroxide, monohydrate → HCID 11179719, compound

HRID 641146Notes

Reaction equation

HRID 641146 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:15][CH2:16][C@:17]2([CH3:23])[CH2:21][O:20]C(=O)[NH:18]2)[CH:5]=[C:6]([CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].O[Li].O>C(O)C.O>[NH2:18][C@:17]([CH3:23])([CH2:16][CH2:15][C:4]1[CH:5]=[C:6]([CH3:14])[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:2]([Br:1])[CH:3]=1)[CH2:21][OH:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66646213HCID 66646213, compound

Product 1

HCID 11179719HCID 11179719, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (R)-4-[2-(3-Bromo-5-methyl-4-pentyloxy-phenyl)-ethyl]-4-methyl-oxazolidin-2-one (58 mg, 0.15 mmol) in ethanol (2 ml) is added a solution of LiOH-hydrate (180 mg, 4.28 mmol) in water (1.5 ml). The mixture is stirred at 90° C. for 2 h. After cooling to RT and extraction with AcOEt (2×20 ml), the organic phase is dried using MgSO4. Evaporation of solvent is followed by reverse phase preparative HPLC (20×250 mm, RP18: 10 μm) using acetonitrile/water/trifluoroacetic acid=900/100/1 as eluent to yield the title compound as white solid. MS (ESI+): m/z=358/360 (MH+).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextraction with AcOEt (2×20 ml)
  3. customthe organic phase is dried
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-30f729dc7f114ed298747ea4975742ac
Source dataset
uspto-grants-2010_04
Patent number
US07696184B2

Reaction notes

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