Lithium Hydroxide → HCID 6480679, compound

HRID 1823941Notes

Reaction equation

[C:1]([NH:9]/[C:10](=[CH:15]\[C:16]1[CH:21]=[CH:20][C:19]([O:22]C2C=CC=CC=2C)=[CH:18][CH:17]=1)/[C:11]([O:13]C)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>O1CCOCC1>[C:1]([NH:9]/[C:10](=[CH:15]\[C:16]1[O:22][C:19]([C:18]2[CH:17]=[CH:4][CH:3]=[CH:2][C:7]=2[CH3:6])=[CH:20][CH:21]=1)/[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1-methyl (Z)-2-(benzoylamino)-3-[4-(2-methylphenoxy)phenyl]prop-2-enoate (104 mg, 0.29 mmol), prepared as described above, in dioxane (5 mL) is added 1 N LiOH (5 mL). The reaction mixture is stirred at 25° C. for 3 hours. The dioxane is then removed under reduced pressure and the remaining reaction mixture poured into a separatory funnel. The aqueous layer is washed with diethyl ether and then acidified (pH=4) by treatment with 10% HCl causing a white precipitate to develop. A portion of ethyl acetate (50 mL) is added and the organic layer is separated, dried over sodium sulfate and concentrated to afford 75 mg of (Z)-2-(benzoylamino)-3-[5-(2-methylphenyl)-2-furyl]prop-2-enoic acid which does not require a further purification.

Workup

customThe dioxane is then removed under reduced pressure
customthe remaining reaction mixture
additionpoured into a separatory funnel
washThe aqueous layer is washed with diethyl ether
additionA portion of ethyl acetate (50 mL) is added
customthe organic layer is separated
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-70bc83f0cd5e438387b3afc84a5edca2
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041690B2

Reaction notes

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