Hydrochloric Acid → HCID 118119372, compound

HRID 2200383Notes

Reaction equation

CC1(C)CO[C:5]2([CH2:9][C@@H:8]([C:10]([NH:12][C:13]3[CH2:20][CH2:19][C:16]4([CH2:18][CH2:17]4)[CH2:15][C:14]=3[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:11])[CH2:7][CH2:6]2)[O:4]C1.Cl>C(O)C>[O:4]=[C:5]1[CH2:6][CH2:7][C@H:8]([C:10]([NH:12][C:13]2[CH2:20][CH2:19][C:16]3([CH2:18][CH2:17]3)[CH2:15][C:14]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:11])[CH2:9]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (S)-ethyl 6-(8,8-dimethyl-6,10-dioxaspiro[4.5]decane-2-carboxamido)spiro[2.5]oct-5-ene-5-carboxylate. (1.5 g, 11.50 mmol) in ethanol (25 ml) was added 1 N hydrochloric acid (7.5 ml) in portion wise manner at 0° C. and the reaction was allowed to stir at 25° C. for overnight. Organic solvent was removed under reduced pressure; the residue was diluted with dichloromethane (50 ml) and water (25 ml). The organic mass was extracted using dichloromethane (3×50 ml). Combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain a crude compound, which was purified by column chromatography over silica gel using ethyl acetate in hexane as eluents to obtain (S)-ethyl 6-(3-oxocyclopentanecarboxamido)spiro[2.5]oct-5-ene-5-carboxylate. (1 g, 85%).

Workup

customOrganic solvent was removed under reduced pressure
additionthe residue was diluted with dichloromethane (50 ml) and water (25 ml)
extractionThe organic mass was extracted
dry with materialCombined organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customto obtain a crude compound, which
customwas purified by column chromatography over silica gel

Sources & evidence

ORD record: ord-46148d58a1a945e59003215a0b580c44
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359367B2

Reaction notes

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