Potassium Phosphate, Dibasic → Benzyl((2R,3S)-2-((4-(((tert-butyldimethylsilyl)oxy)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

HRID 708336Notes

Reaction equation

HRID 708336 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C@@H:16]2[C@H:19]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18](=[O:31])[N:17]2CC2C=CC(OC)=CC=2OC)[N:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].OP([O-])([O-])=O.[K+].[K+]>CC#N.O>[Si:1]([O:8][CH2:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C@@H:16]2[C@H:19]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18](=[O:31])[NH:17]2)[N:11]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24450Potassium Phosphate, DibasicHCID 131733717Benzyl ((2R,3S)-2-((4-(((tert-butyldimethylsilyl)oxy)methyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 131733718Benzyl((2R,3S)-2-((4-(((tert-butyldimethylsilyl)oxy)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamateYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(((tert-butyldimethylsilyl)oxy)methyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate (1.25 g, 2.1 mmol) in CH3CN (20 mL) was added K2S2O8 (0.73 g, 2.7 mmol) followed by a solution of K2HPO4 (0.84 g, 4.8 mmol) in water (10 mL). After stirring at 90° C. for 1 h, more K2S2O8 (0.23 g, 0.84 mmol) was added. After heating at 90° C. for additional 2 h, the reaction mixture was concentrated in vacuo. The residue was extracted with EtOAc (2×30 mL). Combined organic layers were washed with water, brine, dried with Na2SO4, filtered and concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 1-3%) to afford the title compound (0.44 g, 47%) as a pale yellow solid. LCMS: m/z=446.2 (M+1).

Workup

  1. temperatureAfter heating at 90° C. for additional 2 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionThe residue was extracted with EtOAc (2×30 mL)
  4. washCombined organic layers were washed with water, brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 1-3%)

Sources & evidence

ORD record
ord-8c3879479218409eb64608521e034e20
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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