Trifluoroacetic acid → HCID 21706317, compound

HRID 1595048Notes

Reaction equation

HRID 1595048 reaction equation
Cl.C[O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:37]=[CH:36][C:10]([C:11]([C:13]2[C:14]3[CH:35]=[CH:34][CH:33]=[CH:32][C:15]=3[S:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:20][CH:19]=2)=O)=[CH:9][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C1COCC1.ClCCl>[OH:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][C:13]2[C:14]3[CH:35]=[CH:34][CH:33]=[CH:32][C:15]=3[S:16][C:17]=2[C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:22][CH:23]=2)=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21226445Aluminium lithium hydrideHCID 21706337HCID 21706337, compound

Product 1

HCID 21706317HCID 21706317, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the product (1 g, 1.94 mmol) of Example 28 dissolved in anhydrous THF (80 mL) was added LAH (0.47 g, 12.4 mmol) at 0-5° C. under nitrogen. The reaction mixture was stirred for 2 hours and quenched with ice-cold NaOH (0.5 M) solution. The organic layer was extracted with ethyl acetate, combined, dried and concentrated in vacuo. To this residue (0.88 g, 1.8 mmol) dissolved in dichloromethane (˜50 mL) was added triethylsilane (1.73 mL, 10.8 mmol) and TFA (0.42 mL, 5.4 mmol). The reaction mixture was stirred for 1.5 hours before it was washed with dilute NaOH solution and brine until neutral. The combined organic layers were dried with Na2SO4 and concentrated. The residue was purified by column chromatography (20% CH3OH in dichloromethane) to yield 0.53 g (63%) of title compound.

Workup

  1. customquenched with ice-cold NaOH (0.5 M) solution
  2. extractionThe organic layer was extracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated in vacuo
  5. stirringThe reaction mixture was stirred for 1.5 hours before it
  6. washwas washed with dilute NaOH solution and brine until neutral
  7. dry with materialThe combined organic layers were dried with Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (20% CH3OH in dichloromethane)

Sources & evidence

ORD record
ord-23befca2a5ec4464b55a2e9df8cc63c2
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

Loading…