Hydrochloric Acid → HCID 136202030, compound

HRID 2075964Notes

Reaction equation

HRID 2075964 reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[C:11]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:10]=1)C1C=CC=CC=1.Cl>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:26][S:23]([C:11]1[C:12]([C:17]2[N:21]=[C:20]([CH3:22])[O:19][N:18]=2)=[CH:13][C:14]([O:15][CH3:16])=[C:9]([OH:8])[CH:10]=1)(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67096450HCID 67096450, compound

Product 1

HCID 136202030HCID 136202030, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-(4-benzyloxy-2-methanesulfonyl-5-methoxyphenyl)-5-methyl-[1,2,4]oxadiazole and methylene chloride (20 mL) was added titanium(IV) chloride (0.472 g). After stirring at room temperature for 15 minutes, 2 mol/L hydrochloric acid and methylene chloride were added to the mixture. The separated organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10%-100% ethylacetate/hexane, gradient elution) to give the title compound (112 mg).

Workup

  1. concentrationThe separated organic layer was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent: 10%-100% ethylacetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-ebc7db1a1ed8480a8a4bf5bf7835df36
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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