p-Toluenesulfonic acid monohydrate → 3-(5-Bromo-2-methylphenyl)-4-hydroxy-1-azaspiro[4.5]dec-3-ene-2,8-dione

HRID 922134Notes

Reaction equation

O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:36])=[C:18]([C:20]2[C:21](=[O:35])[NH:22][C:23]3([C:33]=2[OH:34])[CH2:32][CH2:31][C:26]2(OCC[O:27]2)[CH2:25][CH2:24]3)[CH:19]=1>CC(C)=O.O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:36])=[C:18]([C:20]2[C:21](=[O:35])[NH:22][C:23]3([CH2:24][CH2:25][C:26](=[O:27])[CH2:31][CH2:32]3)[C:33]=2[OH:34])[CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

192 mg (1.01 mmol) of 4-toluenesulphonic acid monohydrate were added to 2.49 g (6.32 mmol) of 11-(5-bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one (Example 38A) in 26 ml of acetone and 13 ml of water. The reaction mixture was stirred at 80° C. overnight. For work-up, the cold reaction mixture was diluted with water and acetone was removed on a rotary evaporator. The precipitated crude product was extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. Drying gave 1.97 g (89% of theory) of the title compound.

Workup

customFor work-up, the cold reaction mixture
customwas removed on a rotary evaporator
customThe precipitated crude product
extractionwas extracted with ethyl acetate
washThe organic phase was washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
customDrying

Sources & evidence

ORD record: ord-ac91620567144419936d7f7c1802a9fd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278925B2

Reaction notes

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