Methanol → (S)-N-(3-(1H-indol-2-yl)propyl)-2-aminobutanamide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:25])[C@@H:15]([NH:18]C(=O)C(F)(F)F)[CH2:16][CH3:17].O1CCCC1.CO.[OH-].[Na+]>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:25])[C@@H:15]([NH2:18])[CH2:16][CH3:17]Participants
Procedure
A 20 mL cintillation vial was charged with (S)—N-(3-(1H-indol-2-yl)propyl)-2-(2,2,2-trifluoroacetamido)butanamide (48.2 mg, 0.136 mmol), tetrahydrofuran (0.68 mL), and methanol (0.18 mL). 3N Sodium hydroxide (0.14 mL, 0.407 mmol) was added and the resulting mixture stirred at room temperature for 18 h. The resulting mixture was then diluted with dichloromethane and extracted with 1 N HCl. The aqueous layer was neutralized to pH 8 and extracted with dichlormethane. The organic layer was dried with MgSO4, filtered, and concentrated in vacuo. The resulting solid was taken up in water and lyophilized to yield (S)—N-(3-(1H-indol-2-yl)propyl)-2-aminobutanamide. 1H NMR (300 MHz, CDCl3) δ7.52 (d, J=7.6 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.01-7.13 (m, 2H), 6.22 (s, 1H), 3.30-3.49 (m, 3H), 2.72-2.77 (m, 2H), 1.83-1.96 (m, 3H), 1.58-1.66 (m, 1H), and 0.98 (t, J=7.4 Hz, 3H); MS (ES+) 260 (M+1).
Workup
- extractionextracted with 1 N HCl
- extractionextracted with dichlormethane
- dry with materialThe organic layer was dried with MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fb5b7a28abcb443a932699fd33d0d49d
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552032B2
Reaction notes
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