Water → HCID 90871450, compound

HRID 857346Notes

Reaction equation

HRID 857346 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[C:5]1[C:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])(O)[CH2:14][CH2:13][CH2:12][N:6]12.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1)=[C:5]1[CH:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13][CH2:12][N:6]12

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 91454878HCID 91454878, compound

Product 1

HCID 90871450HCID 90871450, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol of Step 5 (70 mg, 0.1 mmol) in CH2Cl2 (2 mL) at r.t. was added 0.25 mL of trifluoroacetic acid and 0.1 mL of triethylsilane. The reaction mixture was stirred at r.t. for 4 hours Water was added, the phases were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated. The residue was swished in EtOAc to provide 22 mg of the title compound as a pale yellow solid.

Workup

  1. additionwas added
  2. customthe phases were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-78ab2ac286324372a8fa8c319693c9ba
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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