Triethylamine → HCID 59512572, compound

HRID 1158139Notes

Reaction equation

HRID 1158139 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:4][C:3]=1[CH3:18].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[Li+].[Cl-].[CH2:35]([C@@H:42]1[CH2:46][O:45][C:44](=[O:47])[NH:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:43]2[C@H:42]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:46][O:45][C:44]2=[O:47])=[O:17])=[CH:4][C:3]=1[CH3:18]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 595125948-(4-Fluoro-3-methylphenyl)octanoic acid

Product 1

HCID 59512572HCID 59512572, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

To a cooled (−10° C.) solution of 8-(4-fluoro-3-methylphenyl)octanoic acid (0.452 g, 1.791 mmol) in 15 mL of THF, were added stepwise triethylamine (0.67 mL, 4.836 mmol) and pivaloyl chloride (0.24 mL, 1.971 mmol). The reaction mixture was stirred at −10° C. for 1 h and then LiCl (0.084 g, 1.971 mmol) and (R)-4-benzyloxazolidin-2-one (0.349 g, 1.971 mmol) were added stepwise. After warming slowly to room temperature and stirring overnight, the reaction mixture was diluted with ethyl acetate (80 mL) and washed with saturated NaHCO3 solution and brine. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-100% dichloromethane/hexanes to give the title compound as colorless oil (0.666 g, 90% yield). GC-MS: tR=9.6 min; m/z 411 (M+).

Workup

  1. temperatureAfter warming slowly to room temperature
  2. stirringstirring overnight
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product was isolated by Flash column chromatography (silica gel column)
  8. washeluting with 0-100% dichloromethane/hexanes

Sources & evidence

ORD record
ord-ec8971d2c83b4fe295204f5accccb32e
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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