1-Piperazinecarboxylic acid, ethyl ester → HCID 66920092, compound

HRID 1185474Notes

Reaction equation

HRID 1185474 reaction equation
C1([NH2+]C2CCCCC2)CCCCC1.[C:14]([O:18][C:19](=[O:38])[CH2:20][CH2:21][CH2:22][C@H:23]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C:24]([O-:26])=O)([CH3:17])([CH3:16])[CH3:15].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:61]([O:63][C:64]([N:66]1[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]1)=[O:65])[CH3:62].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:61]([O:63][C:64]([N:66]1[CH2:67][CH2:68][N:69]([C:24](=[O:26])[C@@H:23]([NH:27][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:22][CH2:21][CH2:20][C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:38])[CH2:70][CH2:71]1)=[O:65])[CH3:62]

Participants

6

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 131731062HCID 131731062, compound

Product 1

HCID 66920092HCID 66920092, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g of (S)-2-Benzyloxycarbonylamino-hexanedioic acid 6-tert-butyl ester dicyclohexyl-ammonium salt, 1.7 g of NEM and 1.2 g of TOTU in 6 ml of DMF, 0.62 g of Piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 16 h. The reaction mixture was diluted saturated aqueous sodium hydrogen carbonate solution and extracted with 150 ml of ethyl acetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 2.2 g.

Workup

  1. extractionextracted with 150 ml of ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-812b746afe4444cb9b372fb204dee065
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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