Trifluoroacetic acid → HCID 53767324, compound

HRID 1003276Notes

Reaction equation

HRID 1003276 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>ClCCl>[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 dichloromethane (5 ml), a solution of trifluoroacetic acid (5 ml) in dichloromethane (5 ml) was added to the solution under ice-cooling with stirring, and the mixture was still stirred for 15 minutes. After reaction at room temperature for 15 minutes, the reaction mixture was concentrated in vacuo. Dichloromethane, water and sodium bicarbonate were added to the resulting residue and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give (S)-4-(2-amino-1,2,3,4-tetrahydronaphthalen-7-yloxy)-N,N-dimethylbutyramide (263 mg) as an oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was still stirred for 15 minutes
  3. customAfter reaction at room temperature for 15 minutes
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. additionDichloromethane, water and sodium bicarbonate were added to the resulting 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. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-93291aade2a04a44aa76961a5f9efb91
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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