Triethylsilane → (3-chloro-4-{1-oxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid

HRID 913170Notes

Reaction equation

HRID 913170 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][C:36]([OH:38])=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:16](O)[C:15]2[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[C:10]=2[C:9]1=[O:34].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][C:36]([OH:38])=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[C:9](=[O:34])[C:10]2[C:11]([O:28][CH2:29][C:30]([F:31])([F:32])[F:33])=[C:12]3[CH:27]=[CH:26][CH:25]=[CH:24][C:13]3=[C:14]([O:18][CH2:19][C:20]([F:21])([F:22])[F:23])[C:15]=2[CH2:16]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 58012477(3-Chloro-4-{1-hydroxy-3-oxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid

Product 1

HCID 24760116(3-chloro-4-{1-oxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (3-chloro-4-{1-hydroxy-3-oxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid (0.235 g, 0.42 mmol) in trifluoroacetic acid (5 ml) cooled to 0° C., was added triethylsilane (0.10 ml, 0.63 mmol). Stirring continued at 0° C. for 5 minutes and then the mixture was evaporated. The crude mixture was purified using MDAP. The clean fractions were evaporated to give a white solid. This was triturated with ether, the resulting white solid collected by filtration (0.008 g, 0.015 mmol). LC/MS: Rt=3.49, [MH]+548.

Workup

  1. customthe mixture was evaporated
  2. customThe crude mixture was purified
  3. customThe clean fractions were evaporated
  4. customto give a white solid
  5. customThis was triturated with ether
  6. filtrationthe resulting white solid collected by filtration (0.008 g, 0.015 mmol)

Sources & evidence

ORD record
ord-ac5464840f64468f9efca5d4f22948dd
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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