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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1841900Generated: October 30, 2026

Hydrochloric Acid → 3-(4,4'-Dichlorobiphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

https://huagongshe.com/reaction/1841900

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantDimethylacetamideHCID 31374—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantMethyl 1-{[(4,4'-dichlorobiphenyl-3-yl)acetyl]amino}-4,4-difluorocyclohexanecarboxylateHCID 86707850—
SolventWaterHCID 962—
Product3-(4,4'-Dichlorobiphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-oneHCID 60168410—

Reaction Steps

3.20 g (5.74 mmol) of the compound from Example 8A were initially charged in a solution of 14 ml of DMA (N,N-dimethylacetamide), a solution of 9 ml of DMA and 1.69 g (2.5 eq.) of potassium tert-butoxide was added dropwise at 20° C. and the mixture was stirred at room temperature for 4 h. The mixture was poured into 200 ml of water and the reaction was adjusted to pH 2 using concentrated aqueous hydrochloric acid, and the resulting residue was filtered off with suction. Purification by flash column chromatography (silica gel; ethyl acetate/n-hexane 1:1) gave 1.50 g (52% of theory) of the title compound of melting point m.p. 156° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946124B2
Source datasetuspto-grants-2015_02
ORD IDord-0b226b9005804d24a12c0a54af2801a8
Source noteuspto-grants-2015_02