Water → HCID 9922328, compound

HRID 1633808Notes

Reaction equation

HRID 1633808 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:11][C:12](=[O:14])[CH3:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].Br[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>CC(CC(C)=O)C>[CH2:9]([O:8][C:6](=[O:7])[C:5]([NH:11][C:12](=[O:14])[CH3:13])([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14041Acetamidomalonic acid diethyl esterHCID 1375215-Bromo-2-methyl-2-pentene

Product 1

HCID 9922328HCID 9922328, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

27.1 g of acetamidomalonic acid diethyl ester are heated for 14 hours with 19.6 g of 5-bromo-2-methyl-2-pentene and 16.6 g of potassium carbonate in 100 ml of MIBK in a water separator. The reaction solution was extracted with 100 ml of water, and the organic phase was concentrated in vacuo. LC-MS analysis of the residue shows that it is a mixture of N-acetyl-D,L-2-amino-6-methyl-5-heptenoic acid ethyl ester (M+H+=228) and acetamido-(4-methyl-3-pentenyl)-malonic acid diethyl ester (M+H+=300) in a ratio of 3:2.

Workup

  1. extractionThe reaction solution was extracted with 100 ml of water
  2. concentrationthe organic phase was concentrated in vacuo
  3. additiona mixture of N-acetyl-D,L-2-amino-6-methyl-5-heptenoic acid ethyl ester (M+H+=228) and acetamido-(4-methyl-3-pentenyl)-malonic acid diethyl ester (M+H+=300) in a ratio of 3:2

Sources & evidence

ORD record
ord-1e2563bcf6cd40e688697535964752d4
Source dataset
uspto-grants-2003_01
Patent number
US06504047B2

Reaction notes

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