Hydrochloric Acid → 11-(5-Bromo-2-methylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one

HRID 922133Notes

Reaction equation

CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:32])=[C:12]([CH2:14][C:15]([NH:17][C:18]2([C:28]([O:30]C)=O)[CH2:27][CH2:26][C:21]3([O:25][CH2:24][CH2:23][O:22]3)[CH2:20][CH2:19]2)=[O:16])[CH:13]=1.Cl>CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:32])=[C:12]([C:14]2[C:15](=[O:16])[NH:17][C:18]3([C:28]=2[OH:30])[CH2:19][CH2:20][C:21]2([O:25][CH2:24][CH2:23][O:22]2)[CH2:26][CH2:27]3)[CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1.92 g (17.08 mmol) of potassium tert-butoxide were added to 3.64 g (8.54 mmol) of methyl 8-{[(5-bromo-2-methylphenyl)acetyl]amino}-1,4-dioxaspiro[4.5]decane-8-carboxylate (Example 27A) in 43 ml of N,N-dimethylformamide. The reaction mixture was stirred at 80° C. for 30 minutes. For work-up, the cold reaction mixture was poured into 500 ml of ice-water and acidified to pH=4 with aqueous hydrochloric acid. The crude product was filtered off. Drying gave 2.49 g (74% of theory) of the title compound which was used without further characterization in the next step.

Workup

customFor work-up, the cold reaction mixture
filtrationThe crude product was filtered off
customDrying

Sources & evidence

ORD record: ord-3013755f143d4aa9af5cf02df95828df
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278925B2

Reaction notes

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