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

HRID 222822

반응식

HRID 222822 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
-20 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-0a19c46d04e844ffb7ec9fc4f180016d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207370B2

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