Lithium hydroxide, monohydrate → HCID 66622459, compound

HRID 852900Notes

Reaction equation

HRID 852900 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O[Li].O>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=3)[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66622253HCID 66622253, compound

Product 1

HCID 66622459HCID 66622459, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 8 (670 mg, 1.59 mmol) in THF (15 mL) at room temperature was added a solution of LiOH.H2O (166 mg, 3.97 mmol) in water (5 mL). After 24 h, the reaction mixture was concentrated, diluted with water and acidified with 2N HCl (pH at 5-6). A precipitate formed, which was separated by filtration, rinsed with water and dried to afford the title compound 9 (600 mg, 1.47 mmol, 93% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): AB system (δA=7.87, δB=7.41, J=8.2 Hz, 4H), 7.68-7.58 (m, 1H), 7.12-6.56 (m, 5H), 5.75 (d, J=5.5 Hz, 1H), 4.53 (d, J=6.3 Hz, 2H), 3.74 and 3.72 (2s, 6H), 3.48-3.30 (m, 2H), 2.80-2.60 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water
  3. customA precipitate formed
  4. customwhich was separated by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-54214ab54592473bbcfacbcd79607f36
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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