Sodium Bicarbonate → 2-Propanol, 2-methyl-, lithium salt (1:1)

HRID 1108594Notes

Reaction equation

HRID 1108594 reaction equation
C([Li:5])CCC.[CH2:6](O[C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][F:32])[C:26](=[O:33])[CH2:25]2)=[C:21]([F:23])[CH:22]=1)=O)[C:7]1[CH:12]=CC=C[CH:8]=1.[CH2:34]([O:38][C:39](=[O:43])CCC)[C@@H:35]1[O:37]C1.C(=O)(O)[O-].[Na+]>C1COCC1.O.CO.C(O)(C)(C)C>[CH3:6][C:7]([CH3:12])([O-:37])[CH3:8].[Li+:5].[F:23][C:21]1[CH:22]=[C:17]([N:16]2[CH2:14][C@H:34]([CH2:35][OH:37])[O:38][C:39]2=[O:43])[CH:18]=[CH:19][C:20]=1[N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][F:32])[C:26](=[O:33])[CH2:25]1

Participants

10

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 22716470HCID 22716470, compoundHCID 178418339Butyllithium

Product 2

HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 54327468HCID 54327468, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-70 °C

Procedure

A solution of lithium tert-butoxide was prepared by addition of n-butyllithium (1.6 m in hexane, 2.9 ml) to a stirred solution of tert-butanol (0.43 g) in anhydrous THF (10 ml) at -10° C. under argon. After cooling to -70° C., a solution of 5-benzyloxycarbonylamino-2-(4-{2-fluoroethyl}-3-oxopiperazin-1-yl)fluorobenzene (1.5 g) in dry THF (15 ml) was added. After 10 minutes, (R)-glycidylbutyrate (0.67 g) in dry THF (15 ml) was added to the resulting mixture, and stirring continued at -70° C. for 15 minutes, before allowing the temperature to rise to ambient over 16 hours. Methanol (10 ml) was added, followed by saturated sodium bicarbonate solution (20 ml) and water (10 ml). The organics were extracted into ethyl acetate (3×25 ml), washed with brine and dried (MgSO4). Solvent was evaporated and the residue purified by chromatography on silica, using as eluant a gradient increasing in polarity from 0 to 3% methanol in dichloromethane. Relevant fractions were combined and evaporated to give (5R)-3-(3-fluoro-4-{4-(2-fluoroethyl)-3-oxopiperazin-1-yl}phenyl)-5-hydroxymethyloxazolidin-2-one (1.07 g).

Workup

  1. waitcontinued at -70° C. for 15 minutes
  2. waitto ambient over 16 hours
  3. extractionThe organics were extracted into ethyl acetate (3×25 ml)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customSolvent was evaporated
  7. customthe residue purified by chromatography on silica
  8. temperaturea gradient increasing in polarity from 0 to 3% methanol in dichloromethane
  9. customevaporated

Sources & evidence

ORD record
ord-e549e4b14c0d4d2484d68f4d83909d5b
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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