Lithium hydroxide, monohydrate → HCID 86671249, compound

HRID 1952547Notes

Reaction equation

HRID 1952547 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:28])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][Si](C(C)(C)C)(C)C)[CH:15]=2)=[N:8][C:7]=1[CH3:29])=[O:5])C.O.[OH-].[Li+]>C1COCC1.O>[OH:20][C:16]1[CH:15]=[C:14]([CH2:13][C:12]([NH:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:29])[N:8]=2)=[O:28])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86671246HCID 86671246, compound

Product 1

HCID 86671249HCID 86671249, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2-{2-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acetylamino}-4-methyl-thiazole-5-carboxylic acid ethyl ester (1.02 g, 2.347 mmol) and lithium hydroxide monohydrate (1 g, 23.83 mmol) in THF (21 mL) and water (7 mL)) was stirred at 25° C. for 16 h. The reaction was quenched by addition of aqueous 2N HCl (25 mL) followed by addition of sodium chloride. The resultant biphasic solution was extracted with 7:3 ethyl acetate/THF (3×125 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give 2-[2-(3-Hydroxy-phenyl)-acetylamino]-4-methyl-thiazole-5-carboxylic acid (0.62 g, 90.4%) as a white solid. MS m/e 293.3 (M+H+).

Workup

  1. customThe reaction was quenched by addition of aqueous 2N HCl (25 mL)
  2. additionfollowed by addition of sodium chloride
  3. extractionThe resultant biphasic solution was extracted with 7:3 ethyl acetate/THF (3×125 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94ee9ddcf6d04cd0ba5b945cd5971bc4
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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