Sulfuric Acid → HCID 178443284, 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].S(=O)(=O)(O)O.[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(OCC)C>[CH2:29]([O:11][C:10](=[O:12])[C@H:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])[NH2:1])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A suspension of L-arginine free base (0.6 g, 3.5 mmol), sulfuric acid (0.31 ml, 7 mmol), and dodecanol (25 ml) were stirred together at 140° C. under nitrogen. After 6 hours, a clear light yellow solution resulted, and TLC indicated the reaction to be complete. The reaction mixture was diluted with diethyl ether (50 ml), and washed with water (3×25 ml). The combined aqueous extracts were washed with diethyl ether (2×25 ml), and basified with 1N KOH solution, upon which a white solid precipitated. Filtration of the suspension and washing of the filtrate with water (3× with 25 ml), acetone (3× with 25 ml) and diethyl ether (3× with 25 ml) gave arginine dodecyl ester. The yield was 86%. Melting point was 125-130° C. NMR gave the expected results for arginine dodecyl ester.
Workup
- customa clear light yellow solution resulted
- customthe reaction
- washwashed with water (3×25 ml)
- washThe combined aqueous extracts were washed with diethyl ether (2×25 ml)
- customprecipitated
- filtrationFiltration of the suspension
- washwashing of the filtrate with water (3× with 25 ml), acetone (3× with 25 ml) and diethyl ether (3× with 25 ml)
Sources & evidence
- ORD record
- ord-0027526028764d9993df4fc6455903f4
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613358B2
Reaction notes
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