Trifluoroacetic acid → 6-Amino-N-(benzyloxy)hexanamide

HRID 1020418Notes

Reaction equation

HRID 1020418 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([NH:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10640621HCID 10640621, compound

Product 1

HCID 595355486-Amino-N-(benzyloxy)hexanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(benzyloxy)-6-(BOC-amino)hexanamide (5.65 g, 16.8 mmol) was dissolved in methylene chloride (40 mL), and the resulting solution thus obtained was cooled at 0° C. The trifluoroacetic acid (2.5 mL, 34 mmol, 2.0 eq.) was added thereto slowly and stirred at room temperature for 24 hrs. The reaction proceeded until no starting material was detectable by TLC. The resulting reaction mixture thus obtained was distilled under a reduced pressure to remove the solvent and thus obtained the title compound quantitatively.

Workup

  1. customthe resulting solution thus obtained
  2. customThe resulting reaction mixture
  3. customthus obtained
  4. distillationwas distilled under a reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-e75fd7cf630f4221b008bdf020268c7e
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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