Ethylmorpholine → [1-(2-Benzyloxycarbonylamino-acetyl)-piperidin-4-yl]carbamic acid butyl ester

HRID 1970627Notes

Reaction equation

HRID 1970627 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.[CH2:24]([O:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH2:25][CH2:26][CH3:27].[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:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][N:34]([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])[CH2:33][CH2:32]1)[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 14349BenzyloxycarbonylglycineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 15676963Piperidin-4-yl-carbamic acid butyl ester

Product 1

HCID 66854689[1-(2-Benzyloxycarbonylamino-acetyl)-piperidin-4-yl]carbamic acid butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 150 mg Z-Gly-OH in 5 ml DMF were added 0.4 ml N-ethylmorpholine, 144 mg piperidin-4-yl-carbamic acid butyl ester and 236 mg TOTU. After stirring for 12 h it was diluted with ethyl acetate and subsequently washed with aqueous LiCl (4%), saturated NaHCO3 and 0.1 M HCl. The crude product thus obtained after evaporation of the solvent was directly used in the next step. Yield: 287 mg.

Workup

  1. washsubsequently washed with aqueous LiCl (4%), saturated NaHCO3 and 0.1 M HCl

Sources & evidence

ORD record
ord-74cce782bc97499799fa024de83b6fd3
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

Loading…