Trifluoroacetic acid → HCID 57656720, compound

HRID 603247Notes

Reaction equation

HRID 603247 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-0da0f3f397a6445abfac14028d2175af
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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