Chloroacetyl chloride → Isopropyl 2-(morpholinoamino)-4-oxo-4,5-dihydrofuran-3-carboxylate

HRID 402736Notes

Reaction equation

HRID 402736 reaction equation
C(O[C:5]1[O:6][CH2:7][C:8](=[O:16])[C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])(C)C.C(OC(C)C)(=O)CC(OC(C)C)=O.ClCC(Cl)=O.[NH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(O)C>[O:39]1[CH2:40][CH2:41][N:36]([NH:35][C:5]2[O:6][CH2:7][C:8](=[O:16])[C:9]=2[C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])[CH2:37][CH2:38]1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 20315N-AminomorpholineHCID 83223Diisopropyl malonateHCID 51050080Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

Product 1

HCID 86708411Isopropyl 2-(morpholinoamino)-4-oxo-4,5-dihydrofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (12.2 g, 53.6 mmol), which similarly prepared according to the procedure described in the Example 74, Third step using diisopropyl malonate and chloroacetyl chloride, in ethanol (45 mL), 4-aminomorpholine (5.7 mL, 59.2 mmol) was added at ambient temperature. The mixture was stirred for 18 h. The solvent was removed under reduced pressure, and the crude product was suspended in methyl tert-butyl ether, then the precipitate was collected by filtration, washed with methyl tert-butyl ether and hexane then dried to afford isopropyl 2-(morpholinoamino)-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (11.2 g, y. 75%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with methyl tert-butyl ether and hexane
  4. customthen dried

Sources & evidence

ORD record
ord-9401091bbd5f4cd7bb2ee7a7c88ee7d2
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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