Ammonia → 3-(Carbamoylmethyl)-5-methylhexanoic acid
Reaction equation
[NH3:1].O.[CH2:3]([CH:7]1[CH2:13][C:12](=[O:14])[O:11][C:9](=[O:10])[CH2:8]1)[CH:4]([CH3:6])[CH3:5]>C(OC)(C)(C)C>[C:9]([CH2:8][CH:7]([CH2:3][CH:4]([CH3:6])[CH3:5])[CH2:13][C:12]([OH:11])=[O:14])(=[O:10])[NH2:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
Aqueous ammonia (308 g of 28% ammonium hydroxide, 5.06 mol), water (431 g), and methyl tert-butyl ether (200 g) are combined and cooled to 15° C. 3-Isobutylglutaric acid anhydride is added and the reaction mixture is allowed to warm to 50° to 60° C. The reaction mixture is cooled to 20°-25° C. The solvent is evaporated and the pH of the solution is adjusted to 1.0 with concentrated hydrochloric acid. Water (200 mL) is added and the mixture is filtered. The solid is washed with water (200 mL). The solid is dried under reduced pressure to give 408 g of (±)-3-(carbamoylmethyl)-5-methylhexanoic acid as an off-white solid. (±)-3-(Carbamoylmethyl)-5-methylhexanoic acid has a melting point in the range of about 107.5° to about 108.5° C. 1H-NMR (DMSO-d6, 200 MHz): δ 0.84 (d, 6H, J=6.5 Hz), 1.07-1.17 (m, 2H), 1.50-1.72 (m, 1H), 1.98-2.25 (m, 5H), 6.75 (s, 1H), 7.30 (s, 1H), 11.6 (s, 1H). IR (KBr): 592.0, 655.7, 700.0, 1010.5, 1133.9, 1214.9, 1241.9, 1278.6, 1294.0, 1427.1, 1461.8, 1585.2, 1668.1, 1700.9, 2514.7, 2622.7, 2962.1, 3220.5, 3367.1 cm-1.
Workup
- temperatureto warm to 50° to 60° C
- temperatureThe reaction mixture is cooled to 20°-25° C
- customThe solvent is evaporated
- additionWater (200 mL) is added
- filtrationthe mixture is filtered
- washThe solid is washed with water (200 mL)
- customThe solid is dried under reduced pressure
Sources & evidence
- ORD record
- ord-aecd8dac43a1414a96ef4a00e65a8739
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616793
Reaction notes
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