Trifluoroacetic acid → HCID 18433517, compound

HRID 2306274Notes

Reaction equation

HRID 2306274 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:7][CH:8]=2)[C:3]=1[NH:20]C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:20][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([O:12][Si:13]([C:16]([CH3:18])([CH3:17])[CH3:19])([CH3:14])[CH3:15])[CH:5]=2)[CH:10]=[CH:11][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 18433490HCID 18433490, compound

Product 1

HCID 18433517HCID 18433517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-1-(tert-butoxycarbonylamino)-7-(tert-butyldimethylsilyloxy)naphthalene, as described above in Step G, (6.0 g, 13.26 mmol) in CH2Cl2 (100 mL) at 0° C. was added TFA (10 mL). After 45 min, the mixture was poured into saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of hexane—5% to 20% CH2Cl2, to yield the above-titled product.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with a gradient of hexane—5% to 20% CH2Cl2

Sources & evidence

ORD record
ord-cfa4507772f04fff9bc5e6b5c79279bd
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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