Ethyl Acetate → HCID 19698551, compound

HRID 862608Notes

Reaction equation

HRID 862608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:23][CH2:24][C:25](OC)=[O:26])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C([O-])(=O)C(C(C([O-])=O)O)O.[K+].[Na+].C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:23][CH2:24][CH2:25][OH:26])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 11949263HCID 11949263, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19698551HCID 19698551, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 100 mg (0.239 mmol) of 3-[4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]oxazol-2-yl]propanoic acid, methyl ester in 10 mL of tetrahydrofuran was cooled to 0° C. with stirring under a nitrogen atmosphere as 0.53 mL of diisobutylaluminum hydride (1M in toluene, 0.523 mmol) was added dropwise over 5 minutes. The reaction was allowed to warm to 25° C. and poured into 100 mL of a saturated solution of sodium potassium tartarate. Ethyl acetate (100 mL) was added and the mixture was stirred until the layers separated (approx. 1 hour). The organic layer was separated and dried over sodium sulfate. Concentration in vacuo gave an oily solid, which was recrystallized from 50% ethyl acetate-isooctane to give 75 mg of a white crystalline solid (mp 123°-124° C.) which was characterized on the basis of its spectral characteristics: 1H-NMR (CDCl3, 300 MHz) ∂ 2.10 (m, 2H), 2.56 (bs, 1H), 3.01 (t, 2H, J=7.0 Hz), 3.07 (s, 3H), 3.80 (t, 2H, J=5.9 Hz), 7.09 (t, 2H, J=8.5 Hz), 7.57 (dd, 2H, J=8.5 and 5.5 Hz), 7.73 (d, 2H, J=8.5 Hz) and 7.89 (d, 2H, J=8.5 Hz). 19F-NMR (CDCl3, 280 MHz) ∂-111.97. LRMS m/z 376 (M+H)+. HRMS calc. for C19H18NO4FS: 376.1019. Observed: 376.1026. Analysis calc. for C19H18NO4FS-C: 60.79, H: 4.83, N: 3.73. Observed-C: 60.53, H: 4.85, N: 3.66.

Workup

  1. additionwas added dropwise over 5 minutes
  2. temperatureto warm to 25° C.
  3. customseparated (approx. 1 hour)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration in vacuo
  7. customgave an oily solid, which
  8. customwas recrystallized from 50% ethyl acetate-isooctane

Sources & evidence

ORD record
ord-33f20b06bb8c42edaf9687d1ad55d4a3
Source dataset
uspto-grants-1998_02
Patent number
US05719163

Reaction notes

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