Formic Acid → HCID 58392751, compound

HRID 446847Notes

Reaction equation

Cl.[C:2]([C@:5]12[C@@:12]3([CH3:30])[CH2:13][C@H:14]([OH:29])[C@@:15]4([F:28])[C@H:24]([C@@H:11]3[CH2:10][C@H:9]1[CH2:8][NH:7][CH2:6]2)[CH2:23][C@H:22]([F:25])[C:21]1[C@:16]4([CH3:27])[CH:17]=[CH:18][C:19](=[O:26])[CH:20]=1)(=[O:4])[CH3:3].[CH3:31][C:32]1[O:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1.C(O)=O>C(#N)C>[C:2]([C@:5]12[C@@:12]3([CH3:30])[CH2:13][C@H:14]([OH:29])[C@@:15]4([F:28])[C@H:24]([C@@H:11]3[CH2:10][C@H:9]1[CH2:8][N:7]([CH2:36][C:35]1[O:38][C:32]([CH3:31])=[CH:33][CH:34]=1)[CH2:6]2)[CH2:23][C@H:22]([F:25])[C:21]1[C@:16]4([CH3:27])[CH:17]=[CH:18][C:19](=[O:26])[CH:20]=1)(=[O:4])[CH3:3]

Participants

Conditions

Temperature: 140 °C

Procedure

In a closed vessel, a mixture of compound 177 (306 mg, 0.692 mmol), 5-methylfurfural (344 μl, 3.46 mmol), TEA (97 μl, 0.692 mmol) and formic acid (266 μl, 6.92 mmol) in acetonitrile (15 ml) is heated under microwave irradiation for 15 minutes at 140° C. LC-MS shows that the reaction is complete. The solution is partitioned between AcOEt and a saturated solution of NaHCO3, the aqueous phase is extracted with AcOEt and the combined organic layers are washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated to give a oil which is purified by silica gel chromatography (eluent AcOEt/petroleum ether 1/1). Trituration with petroleum ether affords the title compound (236 mg, 0.472 mmol, 68.2% yield).

Workup

customThe solution is partitioned between AcOEt
extractiona saturated solution of NaHCO3, the aqueous phase is extracted with AcOEt
washthe combined organic layers are washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customThe solvent is evaporated
customto give a oil which
customis purified by silica gel chromatography (eluent AcOEt/petroleum ether 1/1)

Sources & evidence

ORD record: ord-befcc7f4df174944b526489de15e6e53
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481517B2

Reaction notes

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