1-Methylimidazole → Ethyl 2-octadecanoylamino-3-oxooctadecanoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][NH:6][C:7](=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:2].CN1C=CN=C1.[C:33](Cl)(=[O:49])[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][CH2:47][CH3:48].C(N(CCCC)CCCC)CCC>[Ti](Cl)(Cl)(Cl)Cl.O.ClC1C=CC=CC=1>[C:7]([NH:6][CH:5]([C:33](=[O:49])[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][CH2:47][CH3:48])[C:4]([O:3][CH2:1][CH3:2])=[O:26])(=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -10 °C
Procedure
A chlorobenzene solution (33.0 ml) of N-octadecanoylglycine ethyl ester (2.00 g, 5.41 mmol) and N-methylimidazole (533 mg, 6.49 mmol) was cooled to −10° C., and palmitoyl chloride (1.49 g, 5.41 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 45 minutes at the same temperature, titanium tetrachloride (3.60 g, 18.94 mmol) and tributylamine (4.01 g, 21.64 mmol) were added thereto. The resulting mixture was stirred for 1.5 hours at −10° C. After water (25 ml) was added thereto and the mixture was heated to room temperature, the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 2.52 g of the title compound (yield: 77%).
Workup
- additionwere added
- temperaturethe mixture was heated to room temperature
- customthe organic layer was separated
Sources & evidence
- ORD record
- ord-f41f19ab1b58406282f794f17195aeee
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207370B2
Reaction notes
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