Trifluoroacetic acid → HCID 59846007, compound

HRID 549936Notes

Reaction equation

HRID 549936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C@H:17]3[CH2:22][N:21]([CH:23]4[CH2:28][CH2:27][C:26]([OH:35])([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)[CH2:25][CH2:24]4)[CH2:20][CH2:19][N:18]3C(OC(C)(C)C)=O)=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([C@@H:17]3[NH:18][CH2:19][CH2:20][N:21]([CH:23]4[CH2:28][CH2:27][C:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=5)([OH:35])[CH2:25][CH2:24]4)[CH2:22]3)=[O:16])[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59846022HCID 59846022, compound

Product 1

HCID 59846007HCID 59846007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The faster running isomer of tert-butyl (2R)-2-{[4-(3,4-dichlorophenyl)piperazin-1-yl]carbonyl}-4-(4-hydroxy-4-pyridin-2-ylcyclohexyl)piperazine-1-carboxylate (45 mg) was dissolved in dichloromethane (6 ml). Trifluoroacetic acid (1 ml) was added and the solution stirred at room temperature for 2 hours and allowed to stand over the weekend. The mixture was partitioned between saturated aqueous sodium bicarbonate (10 ml) and dichloromethane (2×100 ml) and combined organics were concentrated in vacuo and adsorbed onto silica for purification by chromatography eluting with 0-15% methanol/dichloromethane. This gave one isomer of 4-((3R)-3-{[4-(3,4-dichlorophenyl)piperazin-1-yl]carbonyl}piperazin-1-yl)-1-pyridin-2-ylcyclohexanol as a light brown solid (31%, 85%).

Workup

  1. customThe mixture was partitioned between saturated aqueous sodium bicarbonate (10 ml) and dichloromethane (2×100 ml)
  2. concentrationcombined organics were concentrated in vacuo
  3. customadsorbed onto silica for purification by chromatography
  4. washeluting with 0-15% methanol/dichloromethane

Sources & evidence

ORD record
ord-bcbd420558e14088a60d15b4c178ca84
Source dataset
uspto-grants-2011_05
Patent number
US07943768B2

Reaction notes

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