Benzyl((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate → Benzyl((2R,3S)-2-((4-formyl-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

HRID 708532Notes

Reaction equation

HRID 708532 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[N:6][N:5]([CH2:8][C@@H:9]2[C@H:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:24])[NH:10]2)[N:4]=1>C1COCC1.O=[Mn]=O>[CH:2]([C:3]1[CH:7]=[N:6][N:5]([CH2:8][C@@H:9]2[C@H:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11](=[O:24])[NH:10]2)[N:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 118411384Benzyl((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 131733826Benzyl((2R,3S)-2-((4-formyl-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl ((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (360 mg, 1.09 mmol) and MnO2 (2.36 g, 27.2 mmol) in THF (11 mL) was stirred at room temperature for 2 h, whereupon the mixture was filtered through celite and concentrated. The resulting material (340 mg, 95%) was used as such in step 3.

Workup

  1. filtrationwas filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f9d1946601814a278f9d7edd5cab84b3
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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