Trifluoroacetic acid → HCID 66855555, compound

HRID 1970621Notes

Reaction equation

HRID 1970621 reaction equation
C([NH:8][C@@H:9]([CH2:13][O:14][CH2:15][CH3:16])[C:10]([OH:12])=O)(OC(C)(C)C)=O.C(N1CCOCC1)C.[CH2:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:31])[CH2:26][CH2:27][CH3:28].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C([O-])(O)=O.[Na+].C(O)(C(F)(F)F)=O>CN(C=O)C.ClCCl>[CH2:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([C:10](=[O:12])[C@@H:9]([NH2:8])[CH2:13][O:14][CH2:15][CH3:16])[CH2:34][CH2:33]1)=[O:31])[CH2:26][CH2:27][CH3:28]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 7525EthylmorpholineHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15058451N-(tert-Butoxy(hydroxy)methylidene)-O-ethylserineHCID 21963126Butyl piperazine-1-carboxylate

Product 1

HCID 66855555HCID 66855555, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 146 mg (S)-N-Boc-2-amino-3-ethoxypropionic acid in 2 ml DMF were added 0.34 ml N-ethylmorpholine, 200 mg 1-butoxycarbonylpiperazine hydrotrifluoroacetate and 219 mg TOTU. After stirring for 12 h it was added saturated aqueous NaHCO3 and the mixture was loaded on a Chem Elut® cartridge, the crude product being eluted with ethyl acetate. The solution was concentrated, the residue obtained dissolved in 5 ml dichloromethane and stirred in the presence of 1 ml TFA. After 12 h stirring it was concentrated and the residue codistilled twice with toluene.

Workup

  1. washthe crude product being eluted with ethyl acetate
  2. concentrationThe solution was concentrated
  3. customthe residue obtained
  4. stirringAfter 12 h stirring it
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-d164dcccd3664fa18f6c707d0f810c28
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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