p-Toluenesulfonic acid monohydrate → HCID 86724295, compound

HRID 594895Notes

Reaction equation

HRID 594895 reaction equation
C(OC([N:8]([C:16]1[O:17][CH2:18][C:19]2([N:40]=1)[C:28]1([CH2:31][O:30][CH2:29]1)[CH2:27][O:26][C:25]1[C:20]2=[CH:21][C:22]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[N:33]=2)=[CH:23][CH:24]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.O>CC#N>[CH3:39][O:38][C:34]1[N:33]=[C:32]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[O:26][CH2:27][C:28]2([CH2:29][O:30][CH2:31]2)[C:19]23[CH2:18][O:17][C:16]([NH2:8])=[N:40]2)[CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86724296HCID 86724296, compound

Product 1

HCID 86724295HCID 86724295, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

The mixture of di-tert-butyl[6′-(6-methoxypyridin-2-yl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]imidodicarbonate (160 mg, 0.289 mmol) and TsOH.H2O (275 mg, 1.45 mmol) in MeCN (3.2 mL) was stirred for 4 hours at 40° C. After dilution with CHCl3, the organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5) and then the residue was washed with EtOAc to afford 6′-(6-methoxypyridin-2-yl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (40 mg).

Workup

  1. washAfter dilution with CHCl3, the organic layer was washed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5)
  5. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-2916697967e74b8ba07f689d268371e5
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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