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

HRID 708523Notes

Reaction equation

HRID 708523 reaction equation
[Si:1]([O:18][CH:19]([C:21]1[CH:25]=[N:24][N:23]([CH2:26][C@@H:27]2[C@H:30]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29](=[O:42])[N:28]2CC2C=CC(OC)=CC=2OC)[N:22]=1)[CH3:20])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OP([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[Si:1]([O:18][CH:19]([C:21]1[CH:25]=[N:24][N:23]([CH2:26][C@@H:27]2[C@H:30]([NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29](=[O:42])[NH:28]2)[N:22]=1)[CH3:20])([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24450Potassium Phosphate, DibasicHCID 131733834Benzyl((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 131733835Benzyl ((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamateYield 68%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate (2.50 g, 3.41 mmol) in ACN/water (2:1, 45 mL) at room temperature was added K2S2O8 (1.57 mg, 5.79 mmol) and K2HPO4 (949 mg, 5.45 mmol). The mixture was heated to 90° C. under nitrogen with stirring for 6 h. The reaction mixture was concentrated in vacuo to remove ACN. To the resulting slurry was added EtOAc and water. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×). The organic portions were combined, dried with Na2SO4, filtered and concentrated in vacuo. Purification of the crude residue via silica gel chromatography (EtOAc-Heptane, 30-60%) afforded the title compound (1.35 g, 68%). LCMS: Rt=1.18 min, m/z=584.3 (M+1) Method 2m_acidic.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove ACN
  3. additionTo the resulting slurry was added EtOAc and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the crude residue via silica gel chromatography (EtOAc-Heptane, 30-60%)

Sources & evidence

ORD record
ord-900fe7a2c61c464b94d3be890a2a15cb
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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