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

HRID 222821

Reaction equation

HRID 222821 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.ClCCl>[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 71%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-45 °C

Procedure

A dichloromethane solution (45.0 ml) of N-acetylglycine ethyl ester (1.50 g, 10.33 mmol) and N-methylimidazole (1.02 mg, 12.40 mmol) was cooled to −45° C., and palmitoyl chloride (2.84 g, 10.33 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 20 minutes at the same temperature, titanium tetrachloride (6.86 mg, 36.16 mmol) and triethylamine (4.18 g, 41.31 mmol) were added thereto. The resulting mixture was stirred for 2 hours at −45° 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 2.81 g of the title compound (yield: 71%).

Workup

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

Sources & evidence

ORD record
ord-22590ac67b1c48e08fa3089c77aa7e75
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Linked notes

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