Sodium Iodide → benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-(azidomethyl)-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

HRID 708480Notes

Reaction equation

HRID 708480 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:29]/[O:30][C:31]2([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[CH2:33][CH2:32]2)/[C:15]([NH:17][C@@H:18]2[C:21](=[O:22])[NH:20][C@@H:19]2[CH2:23]OS(C)(=O)=O)=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[I-].[N-:52]=[N+:53]=[N-:54].[Na+]>CN(C=O)C>[N:52]([CH2:23][C@@H:19]1[C@H:18]([NH:17][C:15](=[O:16])/[C:14](=[N:29]\[O:30][C:31]2([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[CH2:32][CH2:33]2)/[C:12]2[N:13]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[S:10][CH:11]=2)[C:21](=[O:22])[NH:20]1)=[N+:53]=[N-:54]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 118379785benzhydryl 1-[(Z)-[1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-[[(2S,3S)-2-(methylsulfonyloxymethyl)-4-oxoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylate

Product 1

HCID 118379730benzhydryl 1-[(Z)-[2-[[(2R,3S)-2-(azidomethyl)-4-oxoazetidin-3-yl]amino]-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-oxoethylidene]amino]oxycyclopropane-1-carboxylateYield 57.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of benzhydryl 1-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((2S,3S)-2-(((methylsulfonyl)oxy)methyl)-4-oxoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylate (1.3 g, 1.82 mmol) in DMF (20 ml) was added NaI (0.82 g, 5.5 mmol) and sodium azide (0.83 g, 12.8 mmol). After stirring at 60° C. for 6 h, the reaction mixture was quenched with ice cold water and extracted with EtOAc. Combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-heptane) to afford the title compound (689 mg, 57%). LCMS: R=1.02 min, m/z=661.1 (M+1), Method 2m_acidic.

Workup

  1. customthe reaction mixture was quenched with ice cold water
  2. extractionextracted with EtOAc
  3. washCombined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified via silica gel chromatography (EtOAc-heptane)

Sources & evidence

ORD record
ord-e09f6a5926274b1d82123474db18fbc1
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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