Sodium Hydroxide → HCID 19018986, compound

HRID 1110238Notes

Reaction equation

HRID 1110238 reaction equation
[OH-].[Na+].COC(=O)CN(CC(OC)=O)[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:10][CH:9]=1.[C:34]([CH2:37][N:38](C1C=CC(CCCCCCCCCCCCCC)=CC=1)[CH2:39][C:40]([OH:42])=[O:41])([OH:36])=[O:35]>CO>[C:34]([CH2:37][N:38]([C:9]1[CH:8]=[CH:13][CH:12]=[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:10]=1)[CH2:39][C:40]([OH:42])=[O:41])([OH:36])=[O:35]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19018968HCID 19018968, compoundHCID 19389138HCID 19389138, compound

Product 1

HCID 19018986HCID 19018986, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.0 g (3.45 mmol) of 4-tetradecylphenyl aniline (Aldrich Chemical Company), 5.0 ml (0.052 mol) of methyl bromoacetate, 0.95 g (6.9 mmol) of potassium carbonate and 0.5 g (3.45 mmol) of sodium iodide in 15 ml of DMF was stirred and heated at 100° for 45 hours. The solvent was removed at reduced pressure and water was added to the residue. The product was extracted with ethyl acetate and the extract was washed with sodium bisulfite solution, dried and concentrated. The residue was purified by chromatography on silica gel using 25% ethyl acetate-hexane to give 0.7 g of N-(2-methoxy-2-oxoethyl)-N-(4-tetradecylphenyl)glycine methyl ester. This dimethyl ester was hydrolyzed by treatment with 1.5 ml of 6N NaOH in 50 ml of methanol. The mixture was warmed briefly to dissolve the ester and then was kept at room temperature for 3 days. The solvent was removed at reduced pressure and the residue was acidified to pH 2. The product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to a solid which was recrystallized from methanol-water to give 0.26 g, mp 160°-165°, of N-(carboxymethyl)-N-(4-tetradecylphenyl)glycine.

Workup

  1. temperatureThe mixture was warmed briefly
  2. customThe solvent was removed at reduced pressure
  3. extractionThe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated at reduced pressure to a solid which
  6. customwas recrystallized from methanol-water
  7. customto give 0.26 g, mp 160°-165°

Sources & evidence

ORD record
ord-b307cd71c2954d48b20e2a58d89fad63
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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