Cesium carbonate → HCID 59192506, compound

HRID 2384003Notes

Reaction equation

HRID 2384003 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[C:4]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C(#N)C>[C:32]([O:31][C:29](=[O:30])[CH2:28][O:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[C:4]([O:13][S:14]([C:17]([F:20])([F:18])[F:19])(=[O:16])=[O:15])[CH:3]=1)([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 59192511HCID 59192511, compound

Product 1

HCID 59192506HCID 59192506, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of trifluoro-methanesulfonic acid 4-hydroxy-8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester (XXVIII, 177 mg, 0.57 mmol) and cesium carbonate (372 mg, 1.14 mmol) in acetonitrile (5 mL) was added tert-butyl bromoacetate (167 mg, 0.86 mmol) at room temperature under nitrogen. The resulting suspension was stirred for 15 h at room temperature, and then concentrated under vacuum. The residue was diluted with water (10 mL) and ethyl acetate (20 mL). The aqueous layer was separated and extracted with ethyl acetate (20 mL). The combined organic extracts were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by ISCO (40 g) column chromatography, (gradient elution with 5-25% ethyl acetate in hexanes) to provide (5-oxo-3-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (143 mg, 59%) as a white solid: ES(+)-HRMS m/e calcd. for C17H19F3O7S (M+H)+425.0877, obsd. 425.0876.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was diluted with water (10 mL) and ethyl acetate (20 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (20 mL)
  5. washThe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by ISCO (40 g) column chromatography, (gradient elution with 5-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-af6b4bcee2ac4b24bfae29f0e6fe387e
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

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