Lithium hydroxide, monohydrate → HCID 58043685, compound

HRID 519321Notes

Reaction equation

C([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[CH:32]=[C:31]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([N:40]3[CH2:47][CH:46]4[N:48]([CH3:49])[CH:42]([CH2:43][O:44][CH2:45]4)[CH2:41]3)=[CH:36][N:35]=2)[C:30](=[O:50])[N:29]([CH3:51])[CH:28]=1)(=O)C.O[Li].O>CC(O)C.C1COCC1.O>[F:26][C:9]1[CH:8]=[C:7]([C:27]2[CH:32]=[C:31]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([N:40]4[CH2:41][CH:42]5[N:48]([CH3:49])[CH:46]([CH2:45][O:44][CH2:43]5)[CH2:47]4)=[CH:36][N:35]=3)[C:30](=[O:50])[N:29]([CH3:51])[CH:28]=2)[C:6]([CH2:5][OH:4])=[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])[CH:10]=1

Participants

Conditions

Temperature: 30 °C

Procedure

A mixture of 112l (340 mg, 0.489 mmol) and LiOH hydrate (445 mg, 24.45 mmol) in iPrOH (4 mL), THF (4 mL) and H2O (4 mL) was stirred at 30° C. for 1 h. The mixture was evaporated in vacuo, and the residue was purified on prep-HPLC to give 112 as a low yellow solid (105 mg, 32.85%). MS: [M+H]+ 654. 1H NMR (500 MHz, CDCl3) δ 8.46 (d, J=2.5 Hz, 1H), 7.87 (d, J=3.0 Hz, 1H), 7.69 (s, 1H), 7.42 (d, J=2.0 Hz, 1H), 7.23-7.14 (m, 2H), 6.94 (d, J=2.5 Hz, 1H), 6.84 (m, 2H), 4.52 (d, J=11.5 Hz, 1H), 4.31 (m, 2H), 4.12 (m, 5H), 3.89 (m, 3H), 3.69 (s, 3H), 3.43 (m, 4H), 2.84 (s, 2H), 5.62-2.54 (m, 7H), 1.88 (m, 2H), 1.78 (m, 2H)

Workup

customThe mixture was evaporated in vacuo
customthe residue was purified on prep-HPLC

Sources & evidence

ORD record: ord-536fd78ef96a4fdb82fa1926abcd8bbb
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115152B2

Reaction notes

Loading…