Acetamidomalonic acid diethyl ester → HCID 69016854, compound

HRID 1865987Notes

Reaction equation

HRID 1865987 reaction equation
CC([O-])(C)C.[K+].[CH2:7]([O:9][C:10](=[O:21])[CH:11]([NH:17][C:18](=[O:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:8].[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>C1COCC1>[CH2:15]([O:14][C:12](=[O:13])[C:11]([NH:17][C:18](=[O:20])[CH3:19])([C:25]([CH:22]1[CH2:24][CH2:23]1)=[O:26])[C:10]([O:9][CH2:7][CH3:8])=[O:21])[CH3:16]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 77637Cyclopropanecarbonyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 69016854HCID 69016854, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6 eq KOt-Bu in THF at room temperature was added 6 eq 2-acetylamino-malonic acid diethyl ester and after 5 min 1 eq cyclopropane-carbonylchloride. After 15 min, the mixture was concentrated and partitioned between EtOAc and H2O. The organic layer was concentrated to give the desired product in 60% yield.

Workup

  1. concentrationthe mixture was concentrated
  2. custompartitioned between EtOAc and H2O
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-e5fce5d6f9384e819138843a3740c888
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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