Methyl chloroformate → 2-(3-Methoxycarbonylamino-2-oxo-piperidin-1-yl)-propionic acid ethyl ester

HRID 79708Notes

Reaction equation

HRID 79708 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH2:6]([O:8][C:9](=[O:20])[CH:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH2:18])[C:13]1=[O:19])[CH3:11])[CH3:7].CN1CCOCC1>ClCCl>[CH2:6]([O:8][C:9](=[O:20])[CH:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:2]([O:4][CH3:5])=[O:3])[C:13]1=[O:19])[CH3:11])[CH3:7]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 642379182-(3-Amino-2-oxo-piperidin-1-yl)-propionic acid ethyl ester

Product 1

HCID 666201642-(3-Methoxycarbonylamino-2-oxo-piperidin-1-yl)-propionic acid ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl chloroformate (192 μL, 2.5 mmol) was added to a solution of 2-(3-amino-2-oxo-piperidin-1-yl)-propionic acid ethyl ester (353 mg, 1.6 mmol) and 4-methylmorpholine (907 μL, 8.24 mmol) in dichloromethane (10 mL). After 15 minutes the mixture was diluted with dichloromethane (20 mL) and washed with water (10 mL), and aqueous hydrogen chloride (0.5 N, 10 mL). The organic phase was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to provide 2-(3-methoxycarbonylamino-2-oxo-piperidin-1-yl)-propionic acid ethyl ester (332 mg, 1.2 mmol, 75%). C12H20N2O5 calculated 272.1 observed [M+1]+ 273.0; rt=1.82 min.

Workup

  1. washwashed with water (10 mL), and aqueous hydrogen chloride (0.5 N, 10 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-15edbc6a0373406288c59240139e4302
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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