Trifluoroacetic acid → HCID 53767324, compound

HRID 367327Notes

Reaction equation

HRID 367327 reaction equation
C(OC([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[CH:14][CH:15]=2)[CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[CH:14][CH:15]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21967812HCID 21967812, compound

Product 1

HCID 53767324HCID 53767324, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-4-[2-(tert-Butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylbutyramide (396 mg) was dissolved in 5 ml of methylene chloride, a solution of 5 ml of trifluoroacetic acid in 5 ml of methylene chloride was added to the solution with stirring under ice-cooling, and the mixture was stirred for 15 minutes and then subjected to 15 minutes of reaction at room temperature. The reaction solution was concentrated under reduced pressure, methylene chloride, water and sodium bicarbonate were added to the residue, and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated and dried over anhydrous magnesium sulfate. By evaporating the solvent under reduced pressure, 263 mg of (S)-4-(2-amino-1,2,3,4-tetrahydronaphthalen-7-yloxy)-N,N-dimethylbutyramide was obtained in an oily form.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 minutes
  3. customsubjected to 15 minutes of reaction at room temperature
  4. concentrationThe reaction solution was concentrated under reduced pressure, methylene chloride, water and sodium bicarbonate
  5. additionwere added to the residue
  6. stirringthe mixture was stirred at room temperature for 30 minutes
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customBy evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-fd0fe41568954a62885455a1ee27705a
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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