Water → 2-tert-Butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylic acid

HRID 872175Notes

Reaction equation

HRID 872175 reaction equation
[C:1]([C:5]1[S:6][C:7]([C:28]([O:30]C)=[O:29])=[C:8]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([B:18]3[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]3)[C:13]=2[CH3:27])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].O>C(O)(C)C>[C:1]([C:5]1[S:6][C:7]([C:28]([OH:30])=[O:29])=[C:8]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([B:18]3[O:22][C:21]([CH3:23])([CH3:24])[C:20]([CH3:26])([CH3:25])[O:19]3)[C:13]=2[CH3:27])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66634683Methyl 2-tert-Butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylate

Product 1

HCID 666345362-tert-Butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 2-tert-butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylate 109d (1.80 g, 4.05 mmol) and lithium hydroxide (970.0 mg, 40.50 mmol) in isopropyl alcohol (15 mL) and water (15 mL, 830 mmol) was stirred at 40° C. overnight. The reaction mixture was concentrated to ˜50% of original volume, acidified to pH˜2 with conc. hydrochloric acid, and extracted with 9:1 isopropyl acetate/isopropyl alcohol. The extract was dried with anhydrous magnesium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under reduced pressure to afford 2-tert-butyl-4-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamino)methyl)thiazole-5-carboxylic acid 109e (1.74 g, 92%), which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated to ˜50% of original volume
  2. extractionextracted with 9:1 isopropyl acetate/isopropyl alcohol
  3. dry with materialThe extract was dried with anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8b064f8f2b2046be9b832f8bf5fc78c8
Source dataset
uspto-grants-2015_03
Patent number
US08975260B2

Reaction notes

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