Triethylamine → HCID 13932886, compound

HRID 256151

Reaction equation

HRID 256151 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.[O:11]([CH2:18][CH2:19][C:20](O)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:20](=[O:21])[CH2:19][CH2:18][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 815963-Phenoxypropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 13932886HCID 13932886, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Proline methyl ester hydrochloride (3.4 g), 3-phenoxypropionic acid (3.4 g) and triethylamine (2.8 ml) were suspended in dry methylene chloride (30 ml). To the cooled suspension, WSCD HCl (N-ethyl-N',N'-dimethylaminopropyl-carbodiimide hydrochloride) (3.9 g) was added. Under cooling, the mixture was stirred for 1 hour, and after allowing the mixture to warm to room temperature, it was again stirred for 18 horus. The stirred mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under vacuum. The resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: chloroform) to obtain the end compound as an oil (3.7 g).

Workup

  1. temperatureUnder cooling
  2. stirringit was again stirred for 18 horus
  3. washThe stirred mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium bicarbonate and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under vacuum
  6. customThe resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: chloroform)

Sources & evidence

ORD record
ord-808e90378d7b40a881a80eac832fb315
Source dataset
uspto-grants-1987_10
Patent number
US04701465

Linked notes

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