1-Methylimidazole → Ethyl 2-acetylamino-3-oxooctadecanoate

HRID 222822

Reaction equation

HRID 222822 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][NH:6][C:7](=[O:9])[CH3:8])[CH3:2].CN1C=CN=C1.[C:17](Cl)(=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(N(CC)CC)C>[Ti](Cl)(Cl)(Cl)Cl.O.C1(C)C=CC=CC=1>[C:7]([NH:6][CH:5]([C:17](=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:4]([O:3][CH2:1][CH3:2])=[O:10])(=[O:9])[CH3:8]

Participants

8

Reactant 4

HCID 13901-MethylimidazoleHCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 74702Ethyl acetamidoacetate

Product 1

HCID 86638484Ethyl 2-acetylamino-3-oxooctadecanoateYield 66.2%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

A toluene solution (33.0 ml) of N-acetylglycine ethyl ester (1.00 g, 6.89 mmol) and N-methylimidazole (679 mg, 8.27 mmol) was cooled to −20° C., and palmitoyl chloride (1.89 g, 6.89 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 30 minutes at the same temperature, titanium tetrachloride (4.57 mg, 24.12 mmol) and triethylamine (2.79 g, 27.56 mmol) were added thereto. The resulting mixture was stirred for 2 hours at −20° C. Water (20 mL) was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 1.75 g of the title compound (yield: 66%).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated to room temperature
  3. customthe organic layer was separated

Sources & evidence

ORD record
ord-0a19c46d04e844ffb7ec9fc4f180016d
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Linked notes

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