Triethylamine → HCID 19091887, compound

HRID 488305Notes

Reaction equation

HRID 488305 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27]([OH:29])=O)[CH:23]=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH:30]([CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:40][O:39][C:37](=[O:38])[CH2:36][N:30]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:27](=[O:29])[CH2:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 428827Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetateHCID 19091756HCID 19091756, compound

Product 1

HCID 19091887HCID 19091887, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 1.9 g (4.78 mmol) of 3-(octadecyloxy)phenylacetic acid in 40 ml of thionyl chloride was refluxed for 1.5 hours. The excess thionyl chloride was removed at reduced pressure and the resultant acid chloride was dissolved in 40 ml of anhydrous methylene chloride. This solution was added dropwise to an ice bath cooled mixture of 1.0 g (6 mmol) of dimethyl iminodiacetate and 1.4 ml (10 mmol) of triethylamine in 25 ml of methylene chloride. The reaction mixture was kept at room temperature for 17 hours and then was washed with 1N HCl, dried and concentrated to a solid. Purification by chromatography on 150 g of silica gel using 40% ethyl acetate-hexane gave 1.7 g (65% yield, mp 52°-55°) of N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)phenylacetyl]glycine methyl ester.

Workup

  1. customThe excess thionyl chloride was removed at reduced pressure
  2. dissolutionthe resultant acid chloride was dissolved in 40 ml of anhydrous methylene chloride
  3. additionThis solution was added dropwise to an ice bath
  4. temperaturecooled
  5. washwas washed with 1N HCl
  6. customdried
  7. concentrationconcentrated to a solid
  8. customPurification by chromatography on 150 g of silica gel using 40% ethyl acetate-hexane

Sources & evidence

ORD record
ord-18b0a76da0ed46fa8ac15d663df4c3ff
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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