Ethylmorpholine → 4-((S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyryl)-piperazine-1-carboxylic acid propyl ester

HRID 1970654Notes

Reaction equation

HRID 1970654 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]([F:20])([F:19])[F:18])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)=[O:26])[CH2:22][CH3:23].C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:21]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:29][CH2:28]1)=[O:26])[CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22393735Propyl piperazine-1-carboxylateHCID 22955426(S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyric acid

Product 1

HCID 668549974-((S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyryl)-piperazine-1-carboxylic acid propyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 118 mg (S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyric acid in 2 ml DMF were added 70 mg 1-propoxycarbonylpiperazine, 0.18 ml N-ethylmorpholine and 238 mg TOTU. After stirring for 12 h it was diluted with ethyl acetate and extracted with aqueous LiCl (4% w/w), aqueous NaHCO3, 0.1 M HCl and brine. The organic layer was dried over MgSO4 and concentrated to furnish the crude coupling product which was used without further purification in the next step.

Workup

  1. extractionextracted with aqueous LiCl (4% w/w), aqueous NaHCO3, 0.1 M HCl and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customto furnish the crude coupling product which
  5. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-2a9c819f386445f09cffbbda47028fe7
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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