Ethylmorpholine → 4-((S)-2-tert-Butoxycarbonylamino-pent-4-enoyl)-piperazine-1-carboxylic acid ethyl ester

HRID 1970494Notes

Reaction equation

HRID 1970494 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH2:10][CH:11]=[CH2:12])=[O:7])([CH3:4])[CH3:3].C(N1CCOCC1)C.[CH2:24]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])[CH3:25].[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>[CH2:24]([O:26][C:27]([N:29]1[CH2:30][CH2:31][N:32]([C:13](=[O:15])[C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH:11]=[CH2:12])[CH2:33][CH2:34]1)=[O:28])[CH3:25]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734487(2S)-2-(((tert-butoxy)carbonyl)amino)pent-4-enoic acid

Product 1

HCID 668550274-((S)-2-tert-Butoxycarbonylamino-pent-4-enoyl)-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 540 mg Boc-L-Allylglycine in 5 ml DMF were added 0.32 ml N-ethylmorpholine, 0.37 ml ethoxycarbonylpiperazine and 0.83 g TOTU at 0° C. The solution was stirred for 1 h before being diluted with ethyl acetate and extracted subsequently with aqueous LiCl (4%), 0.1 M HCl and half-saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was used without further purification.

Workup

  1. extractionextracted subsequently with aqueous LiCl (4%), 0.1 M HCl and half-saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-2c8d583d638641998ee21dda74104df1
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

Loading…