Lithium Hydroxide → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid

HRID 1177551Notes

Reaction equation

HRID 1177551 reaction equation
[OH-].[Li+].[O:3]1[CH2:8][CH2:7][CH2:6][O:5][CH:4]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([O:26]C)=[O:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)=[C:11]([F:28])[CH:10]=1>C1COCC1>[O:5]1[CH2:6][CH2:7][CH2:8][O:3][CH:4]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)=[C:11]([F:28])[CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67111749HCID 67111749, compound

Product 1

HCID 671115482-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (1M in H2O, 0.80 mL, 0.80 mmol) and methyl 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylate (0.25 g, 0.67 mmol) were stirred in THF (5 mL) for 3 d. The reaction mixture was concentrated under vacuum, the resulting oil was dissolved in a minimum amount of water, and the solution was made acidic with 5 N HCl (aq). The resulting suspension was filtered and the collected solid was dried to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid an off-white solid. MS (ESI) m/z: Calculated: 359.1; Observed: 360.4 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe resulting oil was dissolved in a minimum amount of water
  3. filtrationThe resulting suspension was filtered
  4. customthe collected solid was dried

Sources & evidence

ORD record
ord-8839d4d63f804650b3c837beed1709ca
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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