Ethanol → ethyl (2R)-2-amino-6-acetamidohexanoate
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([CH3:10])=[O:9].O=S(Cl)Cl.[CH3:25][CH2:26]O>>[C:8]([NH:7][CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]([NH2:1])[C:11]([O:13][CH2:25][CH3:26])=[O:12])(=[O:9])[CH3:10]Participants
4
Conditions
- Temperature
- -10 °C
Procedure
Boc-Lys(Ac)-OH (1 equivalent, 0.2 g, 0.69 mmol) was dissolved in EtOH (2 mL). The reaction mixture was cooled at −10° C., and SOCl2 (1.5 equivalent, 76 μl, 1.035 mmol) was added dropwise. The mixture was allowed to warm to room temperature, then heated at 40° C. for 20 h (TLC control). The reaction mixture was concentrated and the crude was purified by flash chromatography (CH2Cl2/MeOH) to afford the compound (120 mg, 80%) as a white solid Rf=0.62 (CH2Cl2/MeOH 70/30).
Workup
- temperatureto warm to room temperature
- temperatureheated at 40° C. for 20 h (TLC control)
- concentrationThe reaction mixture was concentrated
- customthe crude was purified by flash chromatography (CH2Cl2/MeOH)
Sources & evidence
- ORD record
- ord-74d0a55492bf4d2680e2dd777ec9c3c2
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901295B2
Reaction notes
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