HCID 58256124, compound → HCID 67197583, compound

HRID 1019602Notes

Reaction equation

HRID 1019602 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([Br:17])=[C:14](Br)[S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Li]CCCC.[F:23][C:24]([F:34])([F:33])[C:25](C(O)C(F)(F)F)=[O:26]>C1COCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[C:13]([Br:17])=[C:14]([C:25](=[O:26])[C:24]([F:34])([F:33])[F:23])[S:15][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 58256124HCID 58256124, compoundHCID 86653265HCID 86653265, compoundHCID 178418339Butyllithium

Product 1

HCID 67197583HCID 67197583, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The product of Example 1, step (e) (200 mg, 0.52 mmol) was dissolved in 5 mL THF, cooled to −78° C. and treated with BuLi (0.33 mL of 1.6 M). After stirring for 15 minutes at −78° C., trifluoroacetyl 2,2,2-trifluoroethanol (132 uL, 0.68 mmol) was added and the reaction was allowed to warm to room temperature. The reaction was quenched with water (50 uL) and concentrated. The residue was purified by silica gel chromatography to give 73 mg of the sub-title compound.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with water (50 uL)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ce4b7d0ab7794310ade71ecdf04dbc40
Source dataset
uspto-grants-2014_05
Patent number
US08716276B2

Reaction notes

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