4-Methylmorpholine → 2-[3,3-Bis(tert-butoxycarbonylamino)-2-oxo-piperidin-1-yl]-propionic acid ethyl ester

HRID 71752Notes

Reaction equation

HRID 71752 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([NH:32][C:33]([NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])([CH2:37][CH2:38][CH2:39][NH:40][CH:41]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH3:42])[C:34]([OH:36])=O)=[O:31])([CH3:28])([CH3:27])[CH3:26].CN1CCOCC1>CN(C)C=O>[CH2:46]([O:45][C:43](=[O:44])[CH:41]([N:40]1[CH2:39][CH2:38][CH2:37][C:33]([NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:53])[CH3:54])=[O:50])([NH:32][C:30]([O:29][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:31])[C:34]1=[O:36])[CH3:42])[CH3:47]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866488792,2-Bis(tert-butoxycarbonylamino)-5-(1-ethoxycarbonyl-ethylamino)-pentanoic acid

Product 1

HCID 866488782-[3,3-Bis(tert-butoxycarbonylamino)-2-oxo-piperidin-1-yl]-propionic acid ethyl esterYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (1.72 g, 4.5 mmol) was added to a solution of 2,2-bis(tert-butoxycarbonylamino)-5-(1-ethoxycarbonyl-ethylamino)-pentanoic acid (1.31 g, 3.0 mmol) and 4-methylmorpholine in dimethylformamide (50 mL). After 30 minutes the solvent was removed under reduced pressure and the residue was subjected to flash chromatography with eluent of ethyl acetate and hexane. The product-containing fractions were combined and the solvent was removed under reduced pressure to provide 2-[3,3-bis(tert-butoxycarbonylamino)-2-oxo-piperidin-1-yl]-propionic acid ethyl ester (1.11 g, 2.6 mmol, 86%). C20H34N2O7 calculated 414.2 observed [M+1]+ 415.2; rt=2.77 min.

Workup

  1. customAfter 30 minutes the solvent was removed under reduced pressure
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9699ded88fd0420db1cc089c8cbc592d
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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