Hydrochloric Acid → 2-(4-(Tert-butoxycarbonyl)-2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazole-4-carboxylic acid

HRID 549753Notes

Reaction equation

HRID 549753 reaction equation
[OH-].[Li+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][CH:18]=[C:19]([C:21]([O:23]C)=[O:22])[N:20]=2)[CH:12]([CH2:25][O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O.Cl>C1COCC1.CO.O1CCOCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=2)[CH:12]([CH2:25][O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59671612Methyl 2-(4-(tert-butoxycarbonyl)-2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazole-4-carboxylate

Product 1

HCID 596714672-(4-(Tert-butoxycarbonyl)-2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide (15.5 mg, 0.649 mmol) was added to a solution of methyl 2-(4-(tert-butoxycarbonyl)-2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazole-4-carboxylate (0.282 g, 0.649 mmol) in THF (2 mL), MeOH (2 mL), and H2O (1 mL). After 5 h, 4M HCl in 1,4-dioxane (0.200 mL) was added, and the reaction mixture was concentrated under reduced pressure. The material was used without further purification. LC-MS: RT=6.35 min, [M+H]+=421.7.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe material was used without further purification

Sources & evidence

ORD record
ord-08ca8f0c353e4fc48d5fa2d2410d88fd
Source dataset
uspto-grants-2011_05
Patent number
US07943622B2

Reaction notes

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