Trifluoroacetic acid → tert-Butyl (2-{[(5-amino-3-methylthiophen-2-yl)carbonyl](methyl)amino}ethyl)methylcarbamate

HRID 446585Notes

Reaction equation

HRID 446585 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]([N:16]([CH3:28])[CH2:17][CH2:18][N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:15])=[C:11]([CH3:29])[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]([CH3:28])[CH2:17][CH2:18][N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:15])=[C:11]([CH3:29])[CH:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86663470tert-Butyl {2-[({5-[(tert-butoxycarbonyl)amino]-3-methylthiophen-2-yl}carbonyl)(methyl)amino]ethyl}methylcarbamate

Product 1

HCID 86663471tert-Butyl (2-{[(5-amino-3-methylthiophen-2-yl)carbonyl](methyl)amino}ethyl)methylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (350 mg, 0.819 mmol) obtained in Example 89b was dissolved in methylene chloride (8 mL), trifluoroacetic acid (4 mL) was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and moisture was removed from the resulting residue azeotropically with toluene (×2). The resulting residue was dissolved in methylene chloride (8 mL), triethylamine (0.569 mL, 4.10 mmol) and di-tert-butyl dicarbonate (215 mg, 0.983 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2, v/v) to give the title compound (267 mg; yield, 100%) as a light yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and moisture
  2. customwas removed from the resulting residue azeotropically with toluene (×2)
  3. dissolutionThe resulting residue was dissolved in methylene chloride (8 mL)
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2, v/v)

Sources & evidence

ORD record
ord-56fced8d20eb47298b870fc1cf3603ca
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

Loading…