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

HRID 554095Notes

Reaction equation

HRID 554095 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].[O:12]=[CH:13][CH2:14][CH2:15][C:16](O)=O.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C[OH:24]>>[CH:19]1([N:22]2[C:13](=[O:12])[CH2:14][CH2:15][C@H:16]2[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:24])[CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11124-Oxobutanoic acidHCID 69828CyclopropylamineHCID 27580712,4-Dichloro-1-(isocyanomethyl)benzene

Product 1

HCID 674617861-Cyclopropyl-N-[(2,4-dichlorophenyl)methyl]-5-oxoprolinamide

Conditions

Temperature
100 °C

Procedure

To a solution of (2,4-dichlorophenyl)methyl isocyanide (0.047 g, 0.25 mmol) and 4-oxobutanoic acid (15% in water, 0.26 ml, 0.4 mmol) in methanol (1.75 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]-5-oxoprolinamide (0.072 g) as a white solid. LC/MS [M+H]+=326/328, retention time=2.29 minutes.

Workup

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

Sources & evidence

ORD record
ord-2091903b29f24140b6f6ce59f4b9baf6
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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