Water → HCID 19091782, compound

HRID 488252Notes

Reaction equation

HRID 488252 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].C(N(CC)CC)C.[C:30](Cl)(=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].O>C(Cl)Cl>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:22])[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:30](=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:15]=1)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 19091840HCID 19091840, compound

Product 1

HCID 19091782HCID 19091782, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled solution of 3.1 g (10.06 mmol) of N-(3-aminobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester and 2.6 ml (19 mmol) of triethylamine in 60 ml of methylene chloride was added dropwise 3.2 ml (9.6 mmol) of stearoyl chloride. The reaction mixture was stirred in the cold for 30 minutes and then at room temperature for 5 hours. The mixture was poured into water containing 1N HCl and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was purified by chromatography on 70 g of silica gel using 35% ethyl acetate: 10% methylene chloride: 55% hexane and then recrystallization from ethyl acetate-hexane to give 4.5 g (78% yield, mp 76°-79°) of N-(2-ethoxy-2-oxoethyl)-N-[3-(1-oxooctadecylamino)benzoyl]glycine ethyl ester.

Workup

  1. waitat room temperature for 5 hours
  2. extractionthe product was extracted with ethyl acetate
  3. extractionThe dried extract
  4. concentrationwas concentrated to a solid which
  5. customwas purified by chromatography on 70 g of silica gel using 35% ethyl acetate
  6. custom10% methylene chloride: 55% hexane and then recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-730e980d75c7448686e24a4b6a01cba8
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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