Trifluoroacetic acid → HCID 86663439, compound

HRID 446529Notes

Reaction equation

HRID 446529 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]([N:16]([CH3:29])[CH2:17][CH2:18][CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:15])=[C:11]([CH3:30])[CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl>[NH2:8][C:9]1[S:13][C:12]([C:14]([N:16]([CH3:29])[CH2:17][CH2:18][CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:15])=[C:11]([CH3:30])[CH:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86663440HCID 86663440, compound

Product 1

HCID 86663439HCID 86663439, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (129 mg, 0.292 mmol) obtained in Example 30c was dissolved in methylene chloride (3 mL), trifluoroacetic acid (1.5 mL) was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, toluene (×2) was added to the resulting residue, and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in methylene chloride (3 mL), triethylamine (0.318 mL, 2.29 mmol) and di-tert-butyl dicarbonate (244 mg, 1.75 mmol) were added, and the mixture was stirred at room temperature for 15 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v) to give the title compound (78 mg; yield, 78%) as a yellow oily substance.

Workup

  1. customThe solvent was evaporated under reduced pressure, toluene (×2)
  2. additionwas added to the resulting residue
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in methylene chloride (3 mL)
  5. stirringthe mixture was stirred at room temperature for 15 hours
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:2→0:100, v/v)

Sources & evidence

ORD record
ord-63157fd0b80346af854cbf255ad7e375
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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