Trifluoroacetic acid → HCID 57936046, compound

HRID 1912479Notes

Reaction equation

HRID 1912479 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:29])[C@H:16]([NH:21]C(=O)OC(C)(C)C)[C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>ClCCl>[NH2:21][C@H:16]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]([N:12]1[CH2:11][CH2:10][N:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:14][CH2:13]1)=[O:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57936027HCID 57936027, compound

Product 1

HCID 57936046HCID 57936046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 1-(4-(3,4-dichlorophenyl)piperazin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (crude from above) in dichloromethane (5 mL) was added TFA (5 mL). Upon completion of addition, the resulting solution was allowed to stir at rt. for 2 h. After this time, the solvent was removed by rotary evaporation to provide an oil which was partitioned between dichloromethane and 1 N NaOH. The dichloromethane extract was washed with water, dried over MgSO4 and evaporated to provide (R)-2-amino-1-(4-(3,4-dichlorophenyl)piperazin-1-yl)-3,3-dimethylbutan-1-one as an oil (1.09 g).

Workup

  1. additionUpon completion of addition
  2. customAfter this time, the solvent was removed by rotary evaporation
  3. customto provide an oil which
  4. customwas partitioned between dichloromethane and 1 N NaOH
  5. extractionThe dichloromethane extract
  6. washwas washed with water
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-96361f95de764f61bbad6631caa4534f
Source dataset
uspto-grants-2013_12
Patent number
US08609664B2

Reaction notes

Loading…