Methylglyoxal → Diethyl (2-{cyclopropyl[1-({[(2,4-dichlorophenyl)methyl]amino}-carbonyl)-2-oxopropyl]amino}-2-oxoethyl)phosphonate

HRID 546271Notes

Reaction equation

HRID 546271 reaction equation
[CH3:1][C:2]([CH:4]=O)=[O:3].[CH:6]1([NH2:9])[CH2:8][CH2:7]1.[CH2:10]([O:12][P:13]([CH2:18][C:19]([OH:21])=O)([O:15][CH2:16][CH3:17])=[O:14])[CH3:11].[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[CH2:30][N+:31]#[C-:32].C[OH:34]>>[CH:6]1([N:9]([CH:1]([C:32]([NH:31][CH2:30][C:24]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:23]=2[Cl:22])=[O:34])[C:2](=[O:3])[CH3:4])[C:19](=[O:21])[CH2:18][P:13](=[O:14])([O:12][CH2:10][CH3:11])[O:15][CH2:16][CH3:17])[CH2:8][CH2:7]1

Participants

6

Reactant 5

HCID 880MethylglyoxalHCID 887MethanolHCID 36704(Diethoxyphosphinyl)acetic acidHCID 69828CyclopropylamineHCID 27580712,4-Dichloro-1-(isocyanomethyl)benzene

Product 1

HCID 86644398Diethyl (2-{cyclopropyl[1-({[(2,4-dichlorophenyl)methyl]amino}-carbonyl)-2-oxopropyl]amino}-2-oxoethyl)phosphonate

Conditions

Temperature
22 °C

Procedure

To a solution of methylglyoxal (0.153 ml, 1 mmol) in methanol (2 ml) was added cyclopropylamine (0.069 ml, 1 mmol). After stirring at 22° C. for 5 minutes the mixture was treated with [bis(ethyloxy)phosphoryl]acetic acid (0.161 ml, 1 mmol) and (2,4-dichlorophenyl)methyl isocyanide (0.188 g, 1 mmol). The mixture was then stirred for a further 18 hrs at 22° C. following which the solvent was removed in vacuo and the resulting residue was purified by mass-directed automated HPLC to give diethyl (2-{cyclopropyl[1-({[(2,4-dichlorophenyl)methyl]amino}-carbonyl)-2-oxopropyl]amino}-2-oxoethyl)phosphonate (0.043 g) as a brown gum.

Workup

  1. stirringThe mixture was then stirred for a further 18 hrs at 22° C.
  2. customwas removed in vacuo
  3. customthe resulting residue was purified

Sources & evidence

ORD record
ord-34f84fe6ed6944459f93fba061b72513
Source dataset
uspto-grants-2011_05
Patent number
US07935832B2

Reaction notes

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