Lithium hydroxide, monohydrate → HCID 69218670, compound

HRID 272776Notes

Reaction equation

HRID 272776 reaction equation
C[O:2][C:3](=[O:33])[C:4]([C:7]1[CH:8]=[CH:9][C:10]2[NH:16][C:15]3[CH:17]=[C:18]([C:21]4[CH:30]=[CH:29][CH:28]=[C:27]5[C:22]=4[CH:23]=[CH:24][N:25]=[CH:26]5)[CH:19]=[CH:20][C:14]=3[C:13](=[O:31])[NH:12][C:11]=2[CH:32]=1)([CH3:6])[CH3:5].O[Li].O>C1COCC1.O>[CH:26]1[C:27]2[C:22](=[C:21]([C:18]3[CH:19]=[CH:20][C:14]4[C:13](=[O:31])[NH:12][C:11]5[CH:32]=[C:7]([C:4]([CH3:5])([CH3:6])[C:3]([OH:33])=[O:2])[CH:8]=[CH:9][C:10]=5[NH:16][C:15]=4[CH:17]=3)[CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:24][N:25]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69217054HCID 69217054, compound

Product 1

HCID 69218670HCID 69218670, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 806 (85 mg, 0.2 mmol) and LiOH.H2O(42 mg, 1 mmol) in THF (3 mL) and water (5 mL) was heated under reflux for 6 hours. After the reaction mixture cooled to room temperature, it was neutralized to pH=6. The solution was extracted with EtOAc three times, and combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to give the title compound. MS (ESI) m/e 424 (M+H)+, 1H NMR (DMSO-d6, 500 MHz): □ 9.85 (s, 1H), 9.56 (s, 1H), 8.55 (br s, 1H), 8.30 (dd, J=6.08, 3.28 Hz, 1H), 7.99 (s, 1H), 7.85-7.88 (m, 4H), 7.14 (d, J=1.87 Hz, 1H), 7.05 (s, 1H), 7.03 (dd, J=7.96, 1.72 Hz, 1H), 6.95 (d, J=1.25 Hz, 2H), 1.42 (s, 6H).

Workup

  1. temperatureunder reflux for 6 hours
  2. extractionThe solution was extracted with EtOAc three times
  3. washwere washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-56c6cfdd52f94b858d54a2ed5a8df9e3
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

Loading…