Dimethylformamide → 4-(1-Methyl-2-oxo-2-phenylethyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl Ester

HRID 38273

Reaction equation

HRID 38273 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN(C(ON1N=N[C:24]2[CH:25]=[CH:26][CH:27]=N[C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:38]1([CH:44](C)[C:45](O)=[O:46])C=CC=CC=1.[CH3:49]N(C=O)C>C(OCC)C>[CH3:38][CH:44]([N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]1)[C:45](=[O:46])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:49]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 102962-Phenylpropionic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 866310604-(1-Methyl-2-oxo-2-phenylethyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl Ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To N-BOC-piperazine (0.373 g) in DMF (10 ml) was added HATU (1.14 g) followed by 2-phenylpropionic acid (0.30 ml) and the reaction stirred at RT for 16 h followed by 60° C. for 1 h. The reaction was cooled to RT, then diluted with diethyl ether, washed with water (×3), 2M HCl (×2), saturated aq. NaHCO3 (aq) (×2), dried (Na2SO4) and concentrated in vacuo to give the sub-titled compound (0.25 g).

Workup

  1. waitfollowed by 60° C. for 1 h
  2. temperatureThe reaction was cooled to RT
  3. washwashed with water (×3), 2M HCl (×2), saturated aq. NaHCO3 (aq) (×2)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16acc7c4cde945e59cce37a822ebe269
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Linked notes

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