Sodium Iodide → Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxopyridin-1(2H)-yl)methyl)azetidin-3-yl)carbamate

HRID 708372Notes

Reaction equation

HRID 708372 reaction equation
CS(O[CH2:6][C@@H:7]1[C@H:10]([NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C:9](=[O:22])[N:8]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH3:33])(=O)=O.[NH:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]1=[O:40].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C.CCOC(C)=O>[CH3:33][O:32][C:25]1[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=1[CH2:23][N:8]1[C@H:7]([CH2:6][N:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]2=[O:40])[C@H:10]([NH:11][C:12](=[O:13])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]1=[O:22]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 88712-PyridoneHCID 11430Potassium CarbonateHCID 118379363((2S,3S)-3-(((benzyloxy)carbonyl)amino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-2-yl)methyl methanesulfonate

Product 1

HCID 131733738Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxopyridin-1(2H)-yl)methyl)azetidin-3-yl)carbamateYield 35.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

((2S,3S)-3-(((benzyloxy)carbonyl)amino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-2-yl)methyl methanesulfonate (860 mg, 1.80 mmol), pyridin-2(1H)-one (855 mg, 8.99 mmol), K2CO3 (1.74 g, 12.6 mmol) and NaI (746 mg, 4.49 mmol) were slurried in DMF (6.9 mL) and heated to 80° C. with stirring. After 4 h, it was cooled to rt, diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (Acetone-DCM) to afford title compound (304 mg, 35%). LCMS: Rt=0.79 min, m/z=478.2 (M+1) Method 2m_acidic; 1H NMR (500 MHz, CDCl3) δ 7.39-7.28 (m, 6H), 7.07 (d, J=5.9 Hz, 1H), 6.93-6.85 (m, 1H), 6.55 (d, J=9.0 Hz, 1H), 6.40 (d, J=2.4 Hz, 1H), 6.35 (dd, J=8.2, 2.4 Hz, 1H), 6.10-6.02 (m, 1H), 5.87 (d, J=7.8 Hz, 1H), 5.10 (s, 2H), 4.93 (br s, 1H), 4.63 (d, J=14.5 Hz, 1H), 4.27-4.10 (m, 1H), 3.97 (d, J=9.0 Hz, 2H), 3.88 (d, J=14.5 Hz, 1H), 3.78 (s, 3H), 3.76 (s, 3H).

Workup

  1. temperatureit was cooled to rt
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified via silica gel chromatography (Acetone-DCM)

Sources & evidence

ORD record
ord-ab61d141afa148f6813c3dec69d9bd1c
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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