Lithium hydroxide, monohydrate → HCID 70157153, compound

HRID 429766Notes

Reaction equation

HRID 429766 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH:5]([C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=1)[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:15][CH:14]=2)[N:7]=1.O.[OH-].[Li+:38]>C1COCC1.O>[Li+:38].[F:33][C:31]1[CH:32]=[C:27]([CH:5]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]([O:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:19][NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[CH:17][CH:18]=3)[N:7]=2)[CH2:4][C:3]([O-:35])=[O:2])[CH:28]=[C:29]([F:34])[CH:30]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54343880HCID 54343880, compound

Product 1

HCID 70157153HCID 70157153, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 4 (40 mg, 0.088 mmol) in THF (10 ml) and water (5 ml) was stirred at room temperature and lithium hydroxide monohydrate (37 mg, 0.88 mmol) added. The solution was stirred at room temperature for 72 h, then the solvents were removed in vacuo, and the crude white solid partitioned between ethyl acetate (10 ml) and water (10 ml). The water layer was freeze dried and the title compound was obtained as a white solid. 1H NMR (d6 DMSO) δ 8.29 (1H, d, J 5.1 Hz), 7.81 (1H, d, J 5.1 Hz), 7.21 (4H, m), 7.09 (1H, d, J 5.1 Hz), 6.80 (4H, m), .6.52 (1H, t, J 10.0 Hz), 6.42 (1H, t, J 5.8 Hz), 6.39 (1H, d, J 8.6 Hz), 4.42 (1H, t, J 7.9 Hz), 4.34 (2H, s), 2.98 (1H, dd, J 15.6, 8.4 Hz) and 2.77 (1H, dd, J 15.2, 7.5 Hz). MS (ES) m/e 463 [M+H]+.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe crude white solid partitioned between ethyl acetate (10 ml) and water (10 ml)
  3. customdried

Sources & evidence

ORD record
ord-47b64aeb053c4aebbc07437595d73d92
Source dataset
uspto-grants-2001_11
Patent number
US06319922B1

Reaction notes

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