Sodium hydride → (S)-2-[3-(Benzyloxycarbonyl-propyl-amino)-2-oxo-2H-pyridin-1-yl]-butyric acid tert-butyl ester

HRID 2422693Notes

Reaction equation

HRID 2422693 reaction equation
[C:1]([O:5][C:6](=[O:28])[C@@H:7]([N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:11]1=[O:27])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:31](I)[CH2:32][CH3:33]>CN(C=O)C>[C:1]([O:5][C:6](=[O:28])[C@@H:7]([N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:31][CH2:32][CH3:33])[C:11]1=[O:27])[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 57648851(S)-2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester

Product 1

HCID 57648850(S)-2-[3-(Benzyloxycarbonyl-propyl-amino)-2-oxo-2H-pyridin-1-yl]-butyric acid tert-butyl esterYield 1,283.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-butyric acid tert-butyl ester (100 mg, 0.26 mmol) in anhydrous DMF (3 mL) was added NaH (60% dispersion, 10 mg, 0.26 mmol) and the reaction was stirred at ambient temperature for 30 minutes. Propyliodide (30 μL, 0.31 mmol) was added dropwise and the reaction stirred at ambient temperature overnight. The mixture was concentrated in vacuo to a solid and partitioned between EtOAc (10 mL) and water (10 mL). The organic layer was separated, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography (30% EtOAc/hexane) to afford the title compound as a pale green solid (1.43 g, 40%): 1H NMR (400 MHz, CDCl3) δ 0.85-0.95 (6H, m), 1.35 (9H, s), 1.55-1.65 (2H, m), 1.85-1.95 (1H, m), 2.20-2.27 (1H, m), 3.6-3.7 (2H, m), 5.15-5.2 (2H, m), 5.5-5.6 (1H, m), 6.25 (1H, t), 7.25-7.45 (7H, m); M+H 429.4.

Workup

  1. stirringthe reaction stirred at ambient temperature overnight
  2. concentrationThe mixture was concentrated in vacuo to a solid
  3. custompartitioned between EtOAc (10 mL) and water (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-11fb1ce2a5f84cafa045077a9d5edeab
Source dataset
uspto-grants-2011_06
Patent number
US07960415B2

Reaction notes

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