Lithium Hydroxide → HCID 86698149, compound

HRID 632856Notes

Reaction equation

HRID 632856 reaction equation
C([O:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:15](=[N:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[N:14]=[C:13]1[CH2:22][N:23]1[C:27]2[CH:28]=[N:29][CH:30]=[CH:31][C:26]=2[N:25]([CH:32]2[CH2:34][CH2:33]2)[C:24]1=[O:35])(=O)C(C)(C)C.[OH-].[Li+]>C1COCC1.O>[Cl:21][C:17]1[N:16]=[C:15]2[N:14]=[C:13]([CH2:22][N:23]3[C:27]4[CH:28]=[N:29][CH:30]=[CH:31][C:26]=4[N:25]([CH:32]4[CH2:34][CH2:33]4)[C:24]3=[O:35])[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][OH:7])[C:20]2=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57378649HCID 57378649, compound

Product 1

HCID 86698149HCID 86698149, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Compound 3 (0.29 g, 0.58 mmol) was dissolved in THF (15 mL) and lithium hydroxide (40 mg, 1.6 mmol) dissolved in water (5 mL) was added. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured in water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated. The residue was purified by column chromatography using dichloromethane and methanol. The title compound 14 was isolated as a white powder (200 mg, 80%). m/z=414 (M+H)+.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-77b41919f15f4457806f093ed5da545c
Source dataset
uspto-grants-2016_04
Patent number
US09321767B2

Reaction notes

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