Trifluoroacetic acid → HCID 57656720, compound

HRID 2371203Notes

Reaction equation

HRID 2371203 reaction equation
[CH:1]([N:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[C@@H:7]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)=[O:27])[CH2:22][CH2:21]2)=[O:19])[CH2:6]1)([CH2:3][CH3:4])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH:1]([N:5]1[CH2:10][CH2:9][NH:8][C@@H:7]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)=[O:27])[CH2:22][CH2:21]2)=[O:19])[CH2:6]1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57656780HCID 57656780, compound

Product 1

HCID 57656720HCID 57656720, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2R)-4-sec-butyl-2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)carbonyl]piperazine-1-carboxylate (75 mg) was dissolved in dichloromethane (5 ml), trifluoroacetic acid (1 ml) was added and the mixture stirred at room temperature overnight. The mixture was partitioned between dichloromethane (75 ml) and saturated aqueous sodium bicarbonate (15 ml) and the organic layer concentrated in vacuo and adsorbed onto silica for purification by chromatography eluting with 0-20% methanol/dichloromethane. This gave the product as a brittle white solid (41 mg).

Workup

  1. customThe mixture was partitioned between dichloromethane (75 ml) and saturated aqueous sodium bicarbonate (15 ml)
  2. concentrationthe organic layer concentrated in vacuo
  3. customadsorbed onto silica for purification by chromatography
  4. washeluting with 0-20% methanol/dichloromethane

Sources & evidence

ORD record
ord-95ca8e6cd0c84debb61551be094dd560
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

Loading…