Trifluoroacetic acid → HCID 86597377, compound

HRID 898353Notes

Reaction equation

HRID 898353 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([C:15]1[C:19]2[CH:20]=[CH:21][C:22](/[C:24](/[CH2:43][CH3:44])=[CH:25]\[CH2:26][N:27]([O:35]C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[CH:23][C:18]=2[O:17][C:16]=1[CH2:45][CH3:46])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([C:15]1[C:19]2[CH:20]=[CH:21][C:22](/[C:24](/[CH2:43][CH3:44])=[CH:25]\[CH2:26][NH:27][OH:35])=[CH:23][C:18]=2[O:17][C:16]=1[CH2:45][CH3:46])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86597378HCID 86597378, compound

Product 1

HCID 86597377HCID 86597377, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of TFA (5 mL) in methylene chloride (10 mL) was added dropwise to the cold (ice bath) solution of tert-butyl (2Z)-3-(3-benzyl-2-ethyl-1-benzofuran-6-yl)pent-2-enyl[(tert-butoxycarbonyl)oxy]carbamate (4.0 g; 7.45 mmol) in methylene chloride (25 mL). The mixture was stirred at ° C. for 1 hour and at room temperature for 1 hour and solvent evaporated. The residue was extracted with ethyl acetate, washed with sodium bicarbonate solution, water, and evaporated to dryness. The residue was chromatographed on silica gel using 2% ethyl acetate in hexane as an eluent to give the title compound (1.8 g) as an oil. 1HNMR (400 MHz, DMSO-d6): δ 0.85 (t, 2H, J=7.25 Hz), 1.05 (t, 3H, J=7.47 Hz), 1.2-1.25 (m, 6H), 2.35 (q, 2H, J=7.47 Hz), 2.85 (q, 3H, J=7.47 Hz), 3.95 (d, 2H, J=6.59 Hz), 3.96 (s, 2H), 5.55 (t, 1H, J=6.59 Hz), 6.05 (brs, 1H), 6.95 (dd, 1H, J=7.9, 1.32 Hz), 7.22-7.35 (m, 7H).

Workup

  1. waitat room temperature for 1 hour
  2. customsolvent evaporated
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with sodium bicarbonate solution, water
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel using 2% ethyl acetate in hexane as an eluent

Sources & evidence

ORD record
ord-370054ed844c4dda97261e99b31aca67
Source dataset
uspto-grants-2008_04
Patent number
US07351726B2

Reaction notes

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