Octylamine → HCID 86689984, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][S:15]([CH3:17])=[O:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.[CH2:46]([NH2:54])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]>ClCCl>[CH3:17][S:15]([CH2:14][CH2:13][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]([NH:54][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])=[O:12])=[O:16]Participants
Procedure
To a mixture of 2-((tert-butoxycarbonyl)amino)-4-(methylsulfinyl)butanoic acid (10.0 g, 37.7 mmol) and HOBt (6.35 g, 41.5 mmol) in dichloromethane (200 mL) at 0° C. was added triethylamine (10.5 mL, 75.4 mmol) and EDAC (7.95 g, 41.5 mmol). After stirring for 20 minutes octylamine was added and the solution was allowed to warm to room temperature and stirred for 3 days. The reaction was washed with saturated sodium bicarbonate (2×100 mL), 1N HCl (2×100 mL), and brine (1×100 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to give an oil which solidified upon standing. The solid was purified by silica gel chromatography with 0-5% methanol/dichloromethane to give a white solid (13.1 g, 92%). m/z 377 (MH+).
Workup
- additionwas added
- washThe reaction was washed with saturated sodium bicarbonate (2×100 mL), 1N HCl (2×100 mL), and brine (1×100 mL)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customto give an oil which
- customThe solid was purified by silica gel chromatography with 0-5% methanol/dichloromethane
Sources & evidence
- ORD record
- ord-e65e14fa4bfa435bbeeb438f0cd25893
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169203B2
Reaction notes
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