Lithium Hydroxide → HCID 53882576, compound

HRID 1900633Notes

Reaction equation

HRID 1900633 reaction equation
C[O:2][C:3](=[O:35])[C@H:4]([CH2:31][CH2:32][S:33][CH3:34])[NH:5][C:6](=[O:30])[C@H:7]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:8][CH2:9][C@@H:10]([NH:14][C:15](=[O:22])[C@@H:16]1[CH2:20][CH2:19][C:18](=[O:21])[NH:17]1)[CH:11]([CH3:13])[CH3:12].[Li+].[OH-]>CO.O>[NH:17]1[C:18](=[O:21])[CH2:19][CH2:20][C@H:16]1[C:15]([NH:14][C@@H:10]([CH:11]([CH3:13])[CH3:12])[CH2:9][NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:35])=[O:2])[CH2:31][CH2:32][S:33][CH3:34])=[O:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54387736HCID 54387736, compound

Product 1

HCID 53882576HCID 53882576, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The product of Step E was dissolved in 15 mL of methanol and a solution of 60 mg of LiOH in 7 mL of water added. The mixture was stirred for 3 h at room temperature under argon, diluted with water and filtered. The filtrate was neutralized with 10% citric acid and cooled. The product was isolated by filtration and further purified by reverse phase HPLC. Lyophilization gave the title compound as a white solid. 1H-NMR (D2O) δ7.40 (3H, m), 7.29 (2H, m), 4.36 (1H, dd, J=4.9, 8.5 Hz), 4.29 (1H, m), 4.22 (1H, dd, J=6.2, 8.7 Hz), 3.96 (1H, dd, J=7, 13 Hz), 3.33 (1H, dd, J=6.4, 14.3 Hz), 3.20 (3H, m), 2.54 (1H, m), 2.44 (2H, m), 2.39 (1H, m), 2.32 (1H, m), 2.09 (2H, m), 2.06 (3H, s), 1.92 (1H, m), 1.87 (1H, m), 0.92 (3H, d, J=7.8 Hz), 0.90 (3H, d, J=7.8 Hz).

Workup

  1. filtrationfiltered
  2. temperaturecooled
  3. customThe product was isolated by filtration
  4. customfurther purified by reverse phase HPLC

Sources & evidence

ORD record
ord-139014a3fee34c7aa60b81c073a5d8b3
Source dataset
uspto-grants-1996_11
Patent number
US05576293

Reaction notes

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