Stannous Chloride → HCID 15818080, compound

HRID 1419597Notes

Reaction equation

HRID 1419597 reaction equation
[Sn](Cl)Cl.[CH2:4]([NH:11][C@@H:12]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=1)[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-])=O)[CH2:17][CH2:16]1)=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[CH2:4]([NH:11][C@@H:12]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=1)[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH2:27])[CH2:17][CH2:16]1)=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 15818079HCID 15818079, compound

Product 1

HCID 15818080HCID 15818080, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Tin (II) chloride (1.79 g, 9.45 mmol) was added to a solution of (S)-1-[2-benzylamino-3-(3,4-dichlorobenzyloxy)propionyl]-4-(2-nitrophenyl)piperazine (1.03 g, 1.89 mmol) in ethanol (15 mL) and the mixture was stirred at 70° C. for 1 h. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate and washed with aqueous sodium hydroxide (2M, 3 x). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (Aq.) (99:1:0.1) to give (S)-1-[2-benzylamino-3-(3,4-dichlorobenzyloxy)propionyl]-4-(2-aminophenyl)piperazine was a yellow oil (678 mg, 70%). A sample (70 mg) was dissolved in methanolic hydrogen chloride and the solvent was evaporated under reduced pressure. The residue was dissolved in acetonitrile/water (1:1) and freeze-dried to give the title compound as a colorless solid (70 mg); Found: C, 54.06; H, 5.42; N, 9.20. C27H30Cl2N4O2.2HCl.0.5H2O requires: C, 54.47; H, 5.59; N, 9.41%. m/e (ES+) 513 (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with aqueous sodium hydroxide (2M, 3 x)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with CH2Cl2 /MeOH/NH3 (Aq.) (99:1:0.1)

Sources & evidence

ORD record
ord-66993c6189aa4dbe9d5ee0305551f9c6
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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