p-Toluenesulfonic acid → HCID 15058114, compound

HRID 1709376Notes

Reaction equation

HRID 1709376 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][N:6]1[C@H:9]([C@@H:10]2[CH2:14][O:13]C(C)(C)[O:11]2)[C@@H:8]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7]1.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1.C(=O)(O)[O-].[K+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[CH2:5][N:6]1[C@H:9]([C@@H:10]([OH:11])[CH2:14][OH:13])[C@H:8]([NH:17][C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C:7]1=[O:38]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 516893Potassium BicarbonateHCID 18607033HCID 18607033, compound

Product 1

HCID 15058114HCID 15058114, compoundYield 204.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

76.8 g (0.176 mol) of t-butyl (3S,4S)-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-azetidinecarbamate are dissolved in 500 ml of tetrahydrofuran and 350 ml of water and the solution is heated to 60° C. for 24 hours with 13.0 g of p-toluenesulphonic acid. The mixture is cooled, neutralized with 10% aqueous potassium bicarbonate solution and evaporated. The residue is taken up in 300 ml of dioxan and treated with 21.8 g (0.1 mol) of di-t-butyl dicarbonate and 7.63 g of potassium carbonate. The mixture is stirred at room temperature for 24 hours and filtered. The solvent is then removed by evaporation. The crude product is recrystallized from acetonitrile. 61.3 g (88%) of t-butyl (3S, 4S)-1-(2,4-dimethoxybenzyl)-4-[(R)-1,2-dihydroxyethyl]-2-oxo-3-azetidinecarbamate are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. customevaporated
  3. filtrationfiltered
  4. customThe solvent is then removed by evaporation
  5. customThe crude product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c85dfa9fac964c11b5253bfbf01d4bdb
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Reaction notes

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