p-Toluenesulfonic acid → HCID 22643278, compound

HRID 1166580Notes

Reaction equation

HRID 1166580 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][CH2:13][C@@H:14]2[O:19][C:18]3[C:20]([OH:25])=[C:21]([NH2:24])[CH:22]=[CH:23][C:17]=3[O:16][CH2:15]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][CH2:13][CH:14]2[CH2:15][O:16][C:17]3[CH:23]=[CH:22][C:21]4[N:24]=[CH:26][O:25][C:20]=4[C:18]=3[O:19]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86586524HCID 86586524, compound

Product 1

HCID 22643278HCID 22643278, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

[(2R)-7-Amino-8-hydroxy-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methyl-benzenesulfonate hydrochloride (1.05 g, 2.99 mmole) in trimethyl orthoformate (7 mL) was heated to reflux in the presence of 0.20 g of p-toluenesulfonic acid for 3 hours. The solvent was removed under high vacuum to yield a beige solid. The crude product was recrystallized from ethanol to give 0.81 g (75%) of the (R)-enantiomer of the title compound, MS (ESI) m/z 361 (M+H)+.

Workup

  1. customThe solvent was removed under high vacuum
  2. customto yield a beige solid
  3. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-6d610bb8c0ae4bafa1dd415be019ad31
Source dataset
uspto-grants-2003_09
Patent number
US06613913B2

Reaction notes

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