2-Methyleneamino-ethanol → 4-Hydroxy-1-(2-hydroxy-ethyl)-5-oxo-2,5 dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methyl-amide

HRID 2214664Notes

Reaction equation

HRID 2214664 reaction equation
[CH2:1]=[N:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:10][N:11]([CH3:23])[C:12](=[O:22])[CH:13]=[C:14]1[C:18](=[O:19])OC(C)(C)[O:15]1>CO>[Cl:6][C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:10][N:11]([CH3:23])[C:12]([C:13]1[CH2:1][N:2]([CH2:3][CH2:4][OH:5])[C:18](=[O:19])[C:14]=1[OH:15])=[O:22]

Participants

4

Reactant 2

HCID 160500322-Methyleneamino-ethanolHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

Product 1

HCID 547046364-Hydroxy-1-(2-hydroxy-ethyl)-5-oxo-2,5 dihydro-1H-pyrrole-3-carboxylic acid (3,4-dichloro-benzyl)-methyl-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2-methyleneamino-ethanol (1 mL, 0.1 mmol) in MeOH (1 mL) was added N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (0.036 g, 0.1 mmol). The mixture was stirred at 55° C. for 1 h, cooled and purified by preparative HPLC (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA). The title compound was isolated as a white foam (0.018 g, 49% yield). HRMS (M−H) calcd for C15H15N2Cl2O4: 357.04089. found: 357.0396.

Workup

  1. temperaturecooled
  2. custompurified by preparative HPLC (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-ef1bc2f853c04e008553fb1bce227e48
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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