1-Piperazinecarboxylic acid, ethyl ester → HCID 66651778, compound

HRID 1908596Notes

Reaction equation

HRID 1908596 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:10]([OH:12])=O)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:47]([O:49][C:50]([N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)=[O:51])[CH3:48]>CN(C=O)C.C(=O)([O-])O.[Na+]>[CH2:47]([O:49][C:50]([N:52]1[CH2:53][CH2:54][N:55]([C:10](=[O:12])[C@@H:9]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24])[CH2:56][CH2:57]1)=[O:51])[CH3:48]

Participants

6

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 1074725-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 66651778HCID 66651778, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 15 g of (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester, 20.4 g of NEM and 14.5 g of TOTU in 75 ml of DMF, 7.4 g of piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 16 h. The reaction mixture was then diluted with saturated aqueous sodium hydrogen carbonate solution and then extracted with 300 ml of ethyl acetate. The organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution and dried over MgSO4. The solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1). The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 20.6 g.

Workup

  1. extractionextracted with 300 ml of ethyl acetate
  2. washThe organic phase was washed with diluted saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over MgSO4
  4. customThe solvents were removed under reduced pressure
  5. customThe crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1)
  6. additionThe fractions containing the product
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-1ed17ce36e104f2d88f29a5663628cb0
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

Loading…