Lithium Hydroxide → HCID 59050119, compound

HRID 1265227Notes

Reaction equation

[CH:1]1([NH:4][C:5]2[C:8](=[O:9])[C:7](=[O:10])[C:6]=2[NH:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C@@H:26]([C:33]([O:35]C)=[O:34])[NH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:20][CH:19]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:3][CH2:2]1.[OH-].[Li+]>C1COCC1.CO.O>[CH:1]1([NH:4][C:5]2[C:8](=[O:9])[C:7](=[O:10])[C:6]=2[NH:11][C:12]2[CH:13]=[C:14]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH2:25][C@@H:26]([C:33]([OH:35])=[O:34])[NH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:22][CH:23]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

The compound of Example 17 (22.0 mg, 0.04 mmol, 1 equiv) was dissolved in THF/MeOH/H2O 3:1:1 (1 mL) and cooled to 0° C. Solid lithium hydroxide (5.3 mg, 0.22 mol, 5 equiv) was added and the reaction mixture was stirred for two hours at 0° C. The solvents were removed under reduced pressure and the residue was taken up with H2O (2 mL). The resulting solution was acidified with 0.1 N HCl to pH 3 and stirred for 30 min., while a white precipitate was formed. The precipitated title compound was isolated by filtration and dried under vacuum. Yield 15.0 mg, 70.2%. 1H NMR (DMSO, 200 MHz) δ 10.45 (brs, 1H); 9.65 (s, 1H); 8.61 (s, 1H); 7.90-7.71 (m, 1H); 7.65-7.55 (m, 1H); 7.59-7.43 (m, 1H); 7.39-7.17 (m, 3H); 7.02 (d, 1H); 6.84 (d, 1H); 4.49-4.38 (m, 1H); 4.30-4.19 (m, 1H); 4.0 (q, 2H); 3.19-3.02 (m, 1H); 1.17 (t, 3H); 0.85-0.65 (m, 4H). MS (EI) 502 (M+Na), 480 (M+H), 321.

Workup

customThe solvents were removed under reduced pressure
stirringstirred for 30 min., while a white precipitate
customwas formed
customThe precipitated title compound
customwas isolated by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-dd61271195d24314b4dd7867206be188
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545029B2

Reaction notes

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