Hydrochloric Acid → 3-{3-[(Dibenzofuran-2-carbonyl)-amino]phenyl}-acrylic acid

HRID 659104

Reaction equation

C([O:3][C:4](=[O:29])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:16]2[CH:28]=[CH:27][C:19]3[O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:18]=3[CH:17]=2)=[O:15])[CH:8]=1)C.CO.C1COCC1.Cl>CC(OC)(C)C>[CH:17]1[C:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][C:19]=2[CH:27]=[CH:28][C:16]=1[C:14]([NH:13][C:9]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:29])=[O:3])[CH:12]=[CH:11][CH:10]=1)=[O:15]

Participants

Conditions

Temperature: 40 °C

Procedure

The ester (19) (46 mg, 0.12 mmol) was hydrolysed using Method C, except that MeOH (1 mL) and THF (1 mL) were used, and the reaction mixture was heated to 40° C. for 1 hour. After the reaction, TBME was added and the mixture acidified using 6N HCl. The aqueous was extracted with more TBME (×3), EtOAc (×3), dried (MgSO4) and the solvent concentrated in vacuo. The crude solid was triturated with DCM, filtered, washed with heptane and dried to give the title compound. Yield: 34 mg, 81%; LC-MS tr 2.08 min; HPLC Purity: 100%; MS (ES+) m/z 358 (M+H); 1H NMR (400 MHz; DMSO): δ 6.60 (d, 1H), 7.55-7.75 (m, 5H), 7.9 (d, 1H), 7.95-8.05 (m, 2H), 8.25 (s, 1H), 8.30 (d, 1H), 8.40 (d, 1H), 8.95 (s, 1H), 10.65 (s, 1H)

Workup

additionwas added
extractionThe aqueous was extracted with more TBME (×3), EtOAc (×3)
dry with materialdried (MgSO4)
concentrationthe solvent concentrated in vacuo
customThe crude solid was triturated with DCM
filtrationfiltered
washwashed with heptane
customdried

Sources & evidence

ORD record: ord-7ad11f1219ac4ba68972f8d9b5a47837
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080567B2

Linked notes

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