Hydrochloric Acid → HCID 59341084, compound

HRID 14691Notes

Reaction equation

HRID 14691 reaction equation
[OH-].[Li+].C([O:5][C:6]([C:8]1[C:17]2[C:12](=[C:13]([O:20][CH3:21])[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11]([CH2:22][N:23]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]2=[O:33])=[N:10][CH:9]=1)=[O:7])C.Cl>C1COCC1>[O:33]=[C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31](=[O:32])[N:23]1[CH2:22][C:11]1[C:12]2[C:17](=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])[C:8]([C:6]([OH:7])=[O:5])=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59341073HCID 59341073, compound

Product 1

HCID 59341084HCID 59341084, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (1N, 100 mL) was added to a solution of Example 1A (19.6 g, 46.6 mmol) in THF (50 mL), and the reaction was stirred for 16 h. The solution was acidified to pH=3 with 1N HCl. The resulting solid was collected by filtration and dried under vacuum to give 12.6 g (69%) of the title compound. H1-NMR (DMSO-d6): δ 8.90 (s, 1H), 8.58 (t, 1H, J=4.8 Hz), 8.01 (d, 1H, J=2.0 Hz), 7.73 (d, 1H, J=3.6 Hz), 7.66 (d, 1H, J=3.6 Hz), 7.58 (t, 1H, J=3.6 Hz), 7.52 (t, 1H, J=3.6 Hz), 5.10 (d, 2H, J=4.8 Hz), 4.02 (s, 3H), 3.91 (s, 3H). MS (ES) (M+H) calc'd for C21H16N2O6, 393; found 393.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-16919e8637db43cbaa2f93db9d28767e
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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