Lithium hydroxide, monohydrate → HCID 178480084, compound

HRID 407799Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 152c (100 mg, 0.18 mmol) and lithium hydroxide hydrate (84 mg, 2.0 mmol) in THF (8 mL), i-propanol (8 mL) and water (2 mL) was stirred at 40° C. for 0.5 h. The mixture was evaporated under reduced pressure and the residue was diluted with water (5 mL). It was then extracted with ethyl acetate (2×10 mL). The combined extract was concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 152 (6.5 mg, 7%) as a pale yellow solid. MS-ESI: [M+H]+ 515.8. 1H NMR (500 MHz, CDCl3) δ 8.62-8.61 (m, 1H), 8.32 (s, 1H), 8.04 (m, 1H), 7.55-7.53 (m, 4H), 7.50-7.49 (m, 1H), 7.44 (s, 1H), 6.01 (s, 1H), 4.49-4.48 (m, 2H), 3.71 (s, 3H), 1.45 (s, 9H).

Workup

customThe mixture was evaporated under reduced pressure
additionthe residue was diluted with water (5 mL)
extractionIt was then extracted with ethyl acetate (2×10 mL)
extractionThe combined extract
concentrationwas concentrated under reduced pressure
customthe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record: ord-9d0e51da27d943b78625302d653cabd4
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754077B2

Reaction notes

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