Methanol → 1-cyclopropyl-N-[(2,4-dichlorophenyl)methyl]-2-methyl-5-oxoprolinamide

HRID 554142Notes

Reaction equation

HRID 554142 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N+:10]#[C-:11].[C:12]([OH:19])(=O)[CH2:13][CH2:14][C:15]([CH3:17])=O.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.C[OH:25]>>[CH:20]1([N:23]2[C:12](=[O:19])[CH2:13][CH2:14][C@@:15]2([CH3:17])[C:11]([NH:10][CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[O:25])[CH2:22][CH2:21]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11579Levulinic AcidHCID 69828CyclopropylamineHCID 27580712,4-Dichloro-1-(isocyanomethyl)benzene

Product 1

HCID 674589701-cyclopropyl-N-[(2,4-dichlorophenyl)methyl]-2-methyl-5-oxoprolinamide

Conditions

Temperature
100 °C

Procedure

To a solution of (2,4-dichlorophenyl)methyl isocyanide (0.047 g, 0.25 mmol) and levulinic acid (0.041 ml, 0.4 mmol) in methanol (2 ml) was added cyclopropylamine (0.042 ml, 0.6 mmol). The mixture was heated to 100° C. for 30 minutes in a microwave reactor. The solvent was removed in vacuo and the residue was purified by mass-directed automated HPLC to give 1-cyclopropyl-N-[(2,4-dichlorophenyl)methyl]-2-methyl-5-oxoprolinamide (0.054 g) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-cac2b240a23342d3be9e90a8b845edec
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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