Sodium Chloride → HCID 90387114, compound

HRID 2170229Notes

Reaction equation

HRID 2170229 reaction equation
[O:1]=[C:2]([CH3:14])[CH2:3][C:4](ON1C(=O)CCC1=O)=[O:5].[CH3:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][NH:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1.C(N(CC)CC)C.[Cl-].[Na+]>ClCCl>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][N:22]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:4](=[O:5])[CH2:3][C:2](=[O:1])[CH3:14])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 5123089N-Hydroxysuccinimidyl acetoacetateHCID 12201326METHYL 3-(4-METHOXYBENZYLAMINO)PROPANOATE

Product 1

HCID 90387114HCID 90387114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask with stirbar was charged with 2,5-dioxopyrrolidin-1-yl 3-oxobutanoate (6.47 g, 32.5 mmol), methyl 3-(4-methoxybenzylamino)propanoate (prepared as described in Bew, S. et al, Chem Commun. 2006 (41), 4338-40, 7.7 g, 34.5 mmol) and triethylamine (5 mL, 35.9 mmol) in dichloromethane (125 mL). The solution was stirred overnight at ambient temperature, then shaken in a separatory funnel with saturated aqueous sodium chloride. The organics were then washed with saturated aqueous sodium chloride containing 0.1M HCl and dried over anhydrous sodium sulfate. Filtration and solvent removal provided the title compound.

Workup

  1. washThe organics were then washed with saturated aqueous sodium chloride containing 0.1M HCl
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-29625289c34941ca9a8206d0743ae309
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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