2-Dimethylaminopyridine → 2-Tetradecylthioacetamido-1,3-ditetradecylthioacetyloxypropane
Reaction equation
[CH2:1]([CH2:15][C:16]([NH:18][CH:19]([OH:23])[CH2:20][CH2:21]O)=[S:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CN([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29]N=1)C.[CH2:33](CC(O)=S)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>ClCCl>[CH2:1]([CH2:15][C:16]([NH:18][C:19]([O:23][C:16](=[S:17])[CH3:15])([CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH3:33])[CH2:20][CH2:21][CH2:27][CH2:32][CH2:31][CH2:30][CH2:29][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[S:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]Participants
5
Procedure
2-tetradecylthioacetamidopropan-1,3-diol (1 g, 2.77 mmol) (example 5a) was dissolved in dichloromethane (180 ml), then dicyclohexycarbodiimide (1.427 g, 6.91 mmol), dimethylaminopyridine (0.845 g, 6.91 mmol) and tetradecylthioacetic acid (1.995 g, 6.91 mmol) (example 1a) were added in that order. The reaction mixture was stirred at room temperature for 48 hours. The dicyclohexylurea precipitate was filtered and washed with dichloromethane and the filtrate was concentrated. The residue obtained was purified by silica gel chromatography (eluent:dichloromethane-cyclohexane 7:3). The desired compound was obtained as a white powder (yield: 66%).
Workup
- additionwere added in that order
- filtrationThe dicyclohexylurea precipitate was filtered
- washwashed with dichloromethane
- concentrationthe filtrate was concentrated
- customThe residue obtained
- customwas purified by silica gel chromatography (eluent:dichloromethane-cyclohexane 7:3)
Sources & evidence
- ORD record
- ord-90cb11de70d049e9b9a38a897bea8420
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375135B2
Reaction notes
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