Trifluoroacetic acid → HCID 90052146, compound

HRID 2284739Notes

Reaction equation

HRID 2284739 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1([NH:19]C(=O)OC(C)(C)C)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:19][C:13]1([CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90052647HCID 90052647, compound

Product 1

HCID 90052146HCID 90052146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4-(((benzyloxycarbonyl)amino)methyl)tetrahydro-2H-pyran-4-yl)carbamate (G16, 141 mg) in methylene chloride (2 mL), trifluoroacetic acid (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour. The solvent was evaporated under reduced pressure, and then ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain benzyl ((4-aminotetrahydro-2H-pyran-4-yl)methyl)carbamate (G17, 106 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5f8684254c1c43b2a430e70500ed6cbd
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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