Ethylmorpholine → HCID 66856233, compound

HRID 1185485Notes

Reaction equation

HRID 1185485 reaction equation
[NH:1]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH2:2][C:3]([OH:5])=O.C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[CH2:46]([O:50][C:51]([N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)=[O:52])[CH2:47][CH2:48][CH3:49].C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:46]([O:50][C:51]([N:53]1[CH2:58][CH2:57][N:56]([C:3](=[O:5])[CH2:2][NH:1][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:55][CH2:54]1)=[O:52])[CH2:47][CH2:48][CH3:49]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21963126Butyl piperazine-1-carboxylate

Product 1

HCID 66856233HCID 66856233, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.62 g Z-Gly-OH (Benzyloxycarbonylamino-acetic acid) in 100 ml DMF were added 13.7 ml N-ethylmorpholine, 8.8 g TOTU and 5.0 g Piperazine-1-carboxylic acid butyl ester. After stirring for 12 h, aqueous NaHCO3 was added and the reaction mixture was diluted with ethyl acetate and washed with aqueous LiCl (4%) and 0.1 M HCl. The crude product obtained after evaporation of the solvent was purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 6.34 g

Workup

  1. washwashed with aqueous LiCl (4%) and 0.1 M HCl

Sources & evidence

ORD record
ord-2dce2d40e1b54bc7a17ac5ac3703c8f5
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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