Lithium hydroxide, monohydrate → HCID 117771339, compound

HRID 2201545Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([C:41]([O:43]C)=[O:42])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[CH2:1]([O:8][C:9]1[C:10]([C:41]([OH:43])=[O:42])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:37])=[O:38])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinate (540 mg, 0.87 mmol), LiOH.H2O (110 mg, 2.62 mmol) in 1,4-dioxane/H2O (15 mL/5 mL) under N2 was stirred at 100° C. for 1 h. After being filtrated and acidified with HCl to pH=5, the mixture was extracted with EtOAc, the organic phases were dried and concentrated to afford 3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinic acid (520 mg, yield: 98%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.56 (d, J=4.8 Hz, 1H), 7.94˜8.07 (m, 3H), 7.73˜7.85 (m, 3H), 7.50 (d, J=7.2 Hz, 2H), 7.42 (t, J=7.6 Hz, 4H), 7.35 (br s, 1H), 5.30 (s, 2H), 3.20 (s, 3H), 2.94 (s, 3H), 2.82 (d, J=4.4 Hz, 3H). MS (M+H)+: 604.

Workup

filtrationAfter being filtrated
extractionthe mixture was extracted with EtOAc
customthe organic phases were dried
concentrationconcentrated

Sources & evidence

ORD record: ord-47a34655f03c4e0482c2c6c17f9f801b
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364482B2

Reaction notes

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