Lithium hydroxide, monohydrate → HCID 118116876, compound

HRID 1774665Notes

Reaction equation

HRID 1774665 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:39]2[C:44](=[O:45])[C:43]3[S:46][C:47]4[CH2:52][CH2:51][CH2:50][CH2:49][C:48]=4[C:42]=3[CH:41]=[N:40]2)[C:5]([CH2:34][O:35]C(=O)C)=[C:6]([C:8]2[CH:9]=[C:10]([NH:16][C:17]3[N:22]=[C:21]([N:23]4[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH2:24]4)[CH:20]=[CH:19][CH:18]=3)[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.O[Li].O>C1COCC1.CC(O)C.O>[F:1][C:2]1[CH:3]=[C:4]([N:39]2[C:44](=[O:45])[C:43]3[S:46][C:47]4[CH2:52][CH2:51][CH2:50][CH2:49][C:48]=4[C:42]=3[CH:41]=[N:40]2)[C:5]([CH2:34][OH:35])=[C:6]([C:8]2[CH:9]=[C:10]([NH:16][C:17]3[N:22]=[C:21]([N:23]4[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH2:24]4)[CH:20]=[CH:19][CH:18]=3)[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118116658HCID 118116658, compound

Product 1

HCID 118116876HCID 118116876, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 22722550Tetrahydrofuran water isopropanolSolvent

Procedure

A mixture of 115a (73 mg, 0.1 mmol) and LiOH.H2O (40 mg, 1 mmol) in THF/i-PrOH/water (2.0 mL/1.0 mL/1.0 mL) was stirred at rt for 2 h. The mixture was extracted with EA. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC to give 115 (20 mg, 29%) as gray solid. 1H NMR (300 MHz, DMSO-d6, 80° C.): δ 8.42 (s, 1H), 8.40 (s, 1H), 8.00 (s, 1H), 7.77 (d, J=4.5 Hz, 1H), 7.41-7.29 (m, 5H), 6.44 (d, J=3 Hz, 1H), 6.25-6.17 (m, 2H), 5.55-5.50 (m, 1H), 4.35 (s, 2H), 3.98-3.76 (m, 3H), 3.61 (s, 3H), 3.09-2.87 (m, 7H), 1.93-1.87 (m, 6H), 1.71 (bs, 1H), 1.49-1.45 (m, 2H). ESI-LCMS: m/z=682 [C36H36FN7O4S+H]+

Workup

  1. extractionThe mixture was extracted with EA
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-782f11d628a64c3cb8953ab31095209a
Source dataset
uspto-grants-2016_02
Patent number
US09260415B2

Reaction notes

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