Tetrahydrofuran → HCID 59332881, compound

HRID 1879991Notes

Reaction equation

HRID 1879991 reaction equation
[NH2:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C@@H:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8](OCC)=[O:9])=[O:5].C1COCC1.[H-].[Na+]>O>[CH2:13]([C@H:7]1[C:8](=[O:9])[NH:1][C:2]2[N:23]=[CH:22][CH:21]=[CH:20][C:3]=2[C:4](=[O:5])[NH:6]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 59332878HCID 59332878, compound

Product 1

HCID 59332881HCID 59332881, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-Ethyl 2-(2-aminonicotinamido)-3-phenylpropanoate (5.7 g, 18.1 mmol) was dissolved into THF (125 mL) under argon. Sodium hydride (1.07 g, 60% dispersion in oil, 26.8 mmol) was added and the reaction was stirred overnight. Water (5 mL) was carefully added and the resulting white precipitate was collected. The precipitate was dissolved into ethyl acetate (200 mL), washed with water (50 mL) and brine (50 mL), dried over MgSO4 and concentrated to a yellow solid (2.1 g, 44%): ESI MS m/z 268 [C15H13N3O2+H]+.

Workup

  1. customthe resulting white precipitate was collected
  2. dissolutionThe precipitate was dissolved into ethyl acetate (200 mL)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to a yellow solid (2.1 g, 44%)

Sources & evidence

ORD record
ord-b73a2f0b0fe8458099184b30f5379c86
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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