Hydrochloric Acid → HCID 178443295, compound
Reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[C:13](Cl)(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH-].[Na+].Cl>O.C(O)(C)C>[C:13]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
Conditions
- Temperature
- 11.5 °C
Procedure
L-Arginine (1106 g) was added with isopropyl alcohol (6919 g) and water (2964 g), and added dropwise simultaneously with lauroyl chloride (1522 g, Nippon Oil & Fats Co., Ltd.) and 27 wt % NaOH aqueous solution over 2 hours with stirring, while pH and reaction temperature were maintained at 10.5 to 11.5 and 10 to 13° C., respectively. After ripening for 1 hour, the reaction mixture was warmed to 50° C. and adjusted to pH 3.8 with addition of concentrated hydrochloric acid for complete dissolution of the reaction product. Then, the reaction mixture was adjust to pH 6.0 with addition of 27 wt % NaOH aqueous solution to deposit crystals, and the slurry was gradually cooled to 10° C. with stirring. After cooling to 10° C., the slurry was washed with water (10 kg) and isopropyl alcohol (4.4 kg), and the crystals obtained were dried under reduced pressure to give scaly crystals of Nα-mono-lauroyl-L-arginine (2081 g, yield: 92.3%).
Workup
- temperaturethe reaction mixture was warmed to 50° C.
- temperaturethe slurry was gradually cooled to 10° C.
- stirringwith stirring
- temperatureAfter cooling to 10° C.
- washthe slurry was washed with water (10 kg) and isopropyl alcohol (4.4 kg)
- customthe crystals obtained
- customwere dried under reduced pressure
Sources & evidence
- ORD record
- ord-83f5958b068444ccac67dc8dc91e1003
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608250B2
Reaction notes
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