Trifluoroacetic acid → HCID 15366668, compound

HRID 976644Notes

Reaction equation

HRID 976644 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][N:16]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C(=O)OC(C)(C)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([O:15][NH:16][CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19967414HCID 19967414, compound

Product 1

HCID 15366668HCID 15366668, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (42 mL, 544 mmole) was added to a chilled (0° C.) solution of tert-butyl N-benzyloxy-N-(1-ethylpropyl)carbamate (21.6 g, 73.6 mmole) in methylene chloride (300 mL). The reaction was stirred at ambient temperature for about 18 hours then concentrated under vacuum. Saturated aqueous sodium bicarbonate (100 mL) was added to the residue followed by a quantity of solid sodium carbonate sufficient to adjust the pH of the reaction mixture to pH 9. The reaction mixture was extracted with diethyl ether (4×50 mL). The extracts were combined, dried over sodium sulfate then concentrated to provide 10.9 g of N-benzyloxy-N-(1-ethylpropyl)amine as an oil.

Workup

  1. concentrationthen concentrated under vacuum
  2. additionSaturated aqueous sodium bicarbonate (100 mL) was added to the residue
  3. extractionThe reaction mixture was extracted with diethyl ether (4×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-d3c5d2e684ff43229b700b58a35ffc5d
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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