1-Piperazinecarboxylic acid, ethyl ester → HCID 67464426, compound

HRID 553811Notes

Reaction equation

HRID 553811 reaction equation
[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([OH:5])=O.C1C=C2N=NN(O)C2=CC=1.O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.[CH2:48]([O:50][C:51]([N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)=[O:52])[CH3:49].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C.CC(=O)OCC>[CH2:48]([O:50][C:51]([N:53]1[CH2:54][CH2:55][N:56]([C:3](=[O:5])[CH2:2][NH:1][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:57][CH2:58]1)=[O:52])[CH3:49]

Participants

9

Reactant 6

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 14349BenzyloxycarbonylglycineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 67464426HCID 67464426, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Z-Gly-OH (2.09 g), HOBT hydrate (1.57 g), DIPEA (1.76 ml) and EDCI hydrochloride (1.96 g) were dissolved in DCM/DMF (60 ml/15 ml). After 15 min stirring, 1-ethoxycarbonylpiperazine (1.49 ml) was added and the stirring was continued overnight at RT. EA and a NaHCO3 solution were added to the mixture and the phases were separated. The org. phase was washed with a 1M NaHSO4 solution and a NaCl solution, dried (Na2SO4) and evaporated off. After HV drying, 3.5 g of the desired product were obtained.

Workup

  1. waitthe stirring was continued overnight at RT
  2. customthe phases were separated
  3. washphase was washed with a 1M NaHSO4 solution
  4. dry with materiala NaCl solution, dried (Na2SO4)
  5. customevaporated off
  6. customAfter HV drying

Sources & evidence

ORD record
ord-b043c5351d55482e950187310f3370bb
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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