Triethylamine → 2-(1-naphthylmethylene)-3-(N-methyl-N-methoxycarbonylmethylcarbamoyl)propionic acid

HRID 1722903Notes

Reaction equation

HRID 1722903 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[CH2:5][NH:6][CH3:7].C(N(CC)CC)C.[C:16]1([CH:26]=[C:27]2[CH2:32][C:31](=[O:33])[O:30][C:28]2=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>ClCCl>[C:16]1([CH:26]=[C:27]([CH2:32][C:31](=[O:33])[N:6]([CH3:7])[CH2:5][C:4]([O:3][CH3:2])=[O:8])[C:28]([OH:30])=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 543164283-[(Naphthalen-1-yl)methylidene]oxolane-2,5-dione

Product 1

HCID 545054722-(1-naphthylmethylene)-3-(N-methyl-N-methoxycarbonylmethylcarbamoyl)propionic acidYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.40 g of sarcosine methyl ester hydrochloride in 50 ml of dichloromethane were added 1.54 ml of triethylamine and 1.70 g of the 2-(1-naphthylmethylene)succinic anhydride obtained, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was washed successively, with diluted hydrochloric acid, and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: chloroform) to obtain 2.37 g of 2-(1-naphthylmethylene)-3-(N-methyl-N-methoxycarbonylmethylcarbamoyl)propionic acid as a white powder.

Workup

  1. customobtained
  2. washThe reaction mixture was washed successively, with diluted hydrochloric acid
  3. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-a272edaa631946dbbd8e74c1389f891e
Source dataset
uspto-grants-1989_08
Patent number
US04857650

Reaction notes

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