Lithium Hydroxide → HCID 118062278, compound

HRID 920846Notes

Reaction equation

HRID 920846 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:15][N:14]2[N:16]=[C:17]([I:24])[C:18]([C:19]([O:21]CC)=[O:20])=[C:13]2[CH2:12][N:11]1[C:25](=[O:35])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.[Li+].[OH-]>C1COCC1.O>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([NH:26][C:25]([N:11]2[CH:10]([CH2:9][OH:8])[CH2:15][N:14]3[N:16]=[C:17]([I:24])[C:18]([C:19]([OH:21])=[O:20])=[C:13]3[CH2:12]2)=[O:35])=[CH:32][CH:31]=1)#[N:34]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 131734896HCID 131734896, compound

Product 1

HCID 118062278HCID 118062278, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 351E (0.7 g, 1.148 mmol) in THF (10 mL) and water (5 ml) was added LiOH (0.083 g, 3.45 mmol) and the reaction mass was stirred at RT for 24 h. The volatiles were evaporated; the residue was diluted with water (10 mL) and neutralized with an aqueous solution of 1.0 N HCl. The solid product separated was filtered and dried to afford Intermediate 351F (0.4 g, 74%) as an off-white solid which was taken to the next step without further purification. MS(ES): m/z=468 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 12.35-12.80 (br, 1H), 9.33 (s, 1H), 7.69-7.74 (m, 2H), 7.62-7.68 (m, 2H), 5.20-5.30 (m, 1H), 5.10-5.19 (m, 1H), 4.72 (d, J=4.53 Hz, 1H), 4.46 (d, J=18.51 Hz, 1H), 4.27-4.38 (m, 2H), 3.40-3.48 (m, 2H).

Workup

  1. customThe volatiles were evaporated
  2. additionthe residue was diluted with water (10 mL)
  3. customThe solid product separated
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-8e174381114548839eef89fe9add752e
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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