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 708505Notes

Reaction equation

HRID 708505 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-2].[O-2].[Mn+4].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

5

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)carbamateYield 89%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (385 mg, 1.16 mmol) in THF (10 mL) was added manganese dioxide (2.0 g, 23 mmol). After stirring at rt for 12 h, another 1 g of MnO2 was added and stirred for another 1 h. The reaction mixture was filtered over celite with MeOH wash. The filtrate was concentrated in vacuo to give the title compound (340 mg, 89%). The crude residue was used as such in the following step. LCMS: Rt=0.61 min, m/z=330.0 (M+1) Method 2m_acidic.

Workup

  1. stirringstirred for another 1 h
  2. filtrationThe reaction mixture was filtered over celite with MeOH
  3. washwash
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6cf066ca9ec3446bb951706386cdc179
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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