Piperazine → HCID 11128969, compound

HRID 1274107Notes

Reaction equation

HRID 1274107 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(#N)C.O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:13])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 4837PiperazineHCID 85082Tert-butoxycarbonylalanineHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 11128969HCID 11128969, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.15 g of the N-hydroxysuccinimide ester of N-(tert-butoxycarbonyl)-L-alanine are dissolved in 100 ml of DMF and the solution is added dropwise over 6 hours to a mixture of 3.4 g (10 equivalents) of piperazine in 200 ml of DMF. The mixture is concentrated and the residue is taken up in water and extracted three times with 200 ml of dichloromethane each time. The organic phase is dried and the solvent is removed under reduced pressure. The target compound is obtained in a yield of 88%. [TLC: acetonitrile/water/glacial acetic acid 5:1:0.2 Rf =0.42].

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted three times with 200 ml of dichloromethane each time
  3. customThe organic phase is dried
  4. customthe solvent is removed under reduced pressure
  5. customThe target compound is obtained in a yield of 88%

Sources & evidence

ORD record
ord-39ecaf88b6194fccb71a0018aa7f21d9
Source dataset
uspto-grants-2000_12
Patent number
US06156754

Reaction notes

Loading…