Potassium Phosphate, Dibasic → Benzyl ((2R,3S)-2-((5-methyl-1H-tetrazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate

HRID 708358Notes

Reaction equation

HRID 708358 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:9](=[O:10])[C@@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[CH2:22][N:23]1[C:27]([CH3:28])=[N:26][N:25]=[N:24]1.OP([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[CH3:28][C:27]1[N:23]([CH2:22][C@@H:7]2[C@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9](=[O:10])[NH:6]2)[N:24]=[N:25][N:26]=1

Participants

4

Reactant 2

HCID 24450Potassium Phosphate, Dibasic2×HCID 131733729benzyl((2R,3S)-1-(2,4-dimethoxybenzyl)-2-((5-methyl-1H-tetrazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 131733728Benzyl ((2R,3S)-2-((5-methyl-1H-tetrazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamateYield 65%

Reagents, catalysts & solvents 1

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

Procedure

Prepared in an analogous manner to example 4, step 2 using benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-((5-methyl-1H-tetrazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate (221 mg, 0.474 mmol), K2S2O8 (179 mg, 0.663 mmol) and K2HPO4 (107 mg, 0.616 mmol) in ACN:water (2:1, 7.9 mL) at 90° C. for 1.5 h. More K2S2O8 (38.4 mg, 0.142 mmol) and K2HPO4 (21.5 mg, 0.123 mmol) were added and it was heated for an additional 30 min then cooled to rt then concentrated in vacuo. The mixture was diluted with EtOAc, washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 0-10%), to afford the title compound (97 mg, 65%). LCMS: Rt=1.00 min, m/z=317.3 (M+1) Method 2m_acidic.

Workup

  1. temperatureit was heated for an additional 30 min
  2. concentrationthen concentrated in vacuo
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 0-10%)

Sources & evidence

ORD record
ord-b233081c31b04ec092f0dcebc91d4224
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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