Toluene → HCID 68313548, compound

HRID 2404381Notes

Reaction equation

HRID 2404381 reaction equation
[C:1]1([C@H:7]2[CH2:11][C@@H:10]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[F-].[Na+].[F:32][C:33]([F:45])(S(F)(=O)=O)C(O[Si](C)(C)C)=O>CCOC(C)=O>[F:32][C:33]1([F:45])[C@@H:9]2[C@H:8]1[C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:11][C@H:10]2[N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22]

Participants

6

Reactant 4

HCID 1140TolueneHCID 5235Sodium FluorideHCID 2778022Trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetateHCID 68313771HCID 68313771, compound

Product 1

HCID 68313548HCID 68313548, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 54A (419 mg, 1.45 mmol), toluene (0.2 mL), and sodium fluoride (21.3 mg, 0.507 mmol) was heated in a 120° C. oil bath and trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (1.43 mL, 7.24 mmol) was added via syringe pump over 2 hours. After 2 hours, the mixture was diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (25 mL) and brine (10 mL), dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (0-25% EtOAc/hexanes, gradient elution) to provide the title compound (145 mg, 0.427 mmol, 30% yield). MS (DCI) M/Z 357 [M+NH4]+.

Workup

  1. washwashed with saturated aqueous NaHCO3 (25 mL) and brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (0-25% EtOAc/hexanes, gradient elution)

Sources & evidence

ORD record
ord-d2e6982560bc47cfb7c452ce9def6954
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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