Trifluoroacetic acid → HCID 90244054, compound

HRID 529290Notes

Reaction equation

HRID 529290 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]1([NH:11][C:12](=[O:32])[C:13]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])[C@@H:14]([NH:18]C(=O)OC(C)(C)C)[CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:18][C@@H:14]([CH2:15][CH2:16][CH3:17])[C:13]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])[C:12]([NH:11][CH:8]1[CH2:9][CH2:10]1)=[O:32]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 118204534HCID 118204534, compound

Product 1

HCID 90244054HCID 90244054, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2.45 mL, 32.1 mmol) was added to a solution of (S)-tert-butyl 1-(cyclopropylamino)-2,2-diethoxy-1-oxohexan-3-ylcarbamate (2.3 g, 6.41 mmol) in 45 mL CH2Cl2 and the mixture was stirred at room temperature for 18 hours. A saturated NaHCO3 solution was carefully added to the mixture, the aqueous phase was extracted with CH2Cl2 (2×30 mL) and the combined organic phases were dried over Na2SO4. Removal of the solvent in vacuo yielded 1.44 g (3S)-3-Amino-N-cyclopropyl-2,2-diethoxyhexanamide as a pale yellow oil.

Workup

  1. extractionthe aqueous phase was extracted with CH2Cl2 (2×30 mL)
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-2e2a73cb0f83467bbaf947a96cea3413
Source dataset
uspto-grants-2016_05
Patent number
US09346853B2

Reaction notes

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