Methanol → (S)-2-amino-N-(3-(1-methyl-1H-indol-2-yl)propyl)butanamide

HRID 1039024Notes

Reaction equation

HRID 1039024 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:26])[C@@H:16]([NH:19]C(=O)C(F)(F)F)[CH2:17][CH3:18].O1CCCC1.CO.[OH-].[Na+]>ClCCl>[NH2:19][C@@H:16]([CH2:17][CH3:18])[C:15]([NH:14][CH2:13][CH2:12][CH2:11][C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86654755N-(3-(1-methyl-1H-indol-2-yl)propyl)-2-(S)-(2,2,2-trifluoro-acetylamino)butanamide

Product 1

HCID 53252316(S)-2-amino-N-(3-(1-methyl-1H-indol-2-yl)propyl)butanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 20 mL cintillation vial was charged with N-(3-(1-methyl-1H-indol-2-yl)propyl)-2-(S)-(2,2,2-trifluoro-acetylamino)butanamide (57.0 mg, 0.154 mmol), tetrahydrofuran (0.77 mL), and methanol (0.20 mL). 3N Sodium hydroxide (0.15 mL, 0.450 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, filter, and concentrate in vacuo. The resulting solid was taken up in water and lyophilized to yield (S)-2-amino-N-(3-(1-methyl-1H-indol-2-yl)propyl)butanamide. 1H NMR (300 MHz, CD3OD) δ 7.42 (d, J=7.7 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 7.05-7.11 (m, 1H), 6.94-7.02 (m, 1H), 6.23 (s, 1H), 3.60-3.75 (m, 4H), 3.31-3.46 (m, 2H), 2.69-2.86 (m, 2H), 1.91-2.03 (m, 2H), 1.71-1.89 (m, 2H), and 1.02 (t, J=7.4 Hz, 3H); MS (ES+) 274 (M+1).

Workup

  1. extractionextracted with 1 N HCl
  2. extractionextracted with dichlormethane
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-bb2db21c5dc34ae2b8976833cdbe196e
Source dataset
uspto-grants-2013_10
Patent number
US08552032B2

Reaction notes

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