Boron trifluoride etherate → HCID 18188628, compound

HRID 1358125Notes

Reaction equation

HRID 1358125 reaction equation
[F:1][CH:2]([F:24])[O:3][CH:4]([C:9]1[CH:23]=[CH:22][C:12]2[C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[O:15][CH:16](O)[C:11]=2[CH:10]=1)[S:5]([NH2:8])(=[O:7])=[O:6].[CH2:25]([Si](C)(C)C)[CH:26]=[CH2:27].B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>ClCCl>[F:24][CH:2]([F:1])[O:3][CH:4]([C:9]1[CH:23]=[CH:22][C:12]2[C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[O:15][CH:16]([CH2:27][CH:26]=[CH2:25])[C:11]=2[CH:10]=1)[S:5]([NH2:8])(=[O:6])=[O:7]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 516892Sodium BicarbonateHCID 18188609HCID 18188609, compound

Product 1

HCID 18188628HCID 18188628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 27G (0.14 g, 0.39 mmol) in dichloromethane (10 mL) at −78° C. was treated with allyltrimethylsilane (0.13 g, 1.16 mmol) and borontrifluoride etherate (0.156 g, 1.16 mmol), stirred for 1 hour, and treated with saturated sodium bicarbonate (10 mL) to provide two laters. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)Q1MS) m/z 380 (M−H)−.

Workup

  1. customto provide two laters
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe extract was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 20-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a7bbf72155324dc08288e9497a91b848
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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