Potassium Permanganate → HCID 86671247, compound

HRID 1952544Notes

Reaction equation

HRID 1952544 reaction equation
[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([NH:16][C:17]2[S:18][C:19]([CH:23]=[O:24])=[C:20]([Cl:22])[N:21]=2)=[O:15])[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:28].[K+]>C(O)(C)(C)C.O>[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([NH:16][C:17]2[S:18][C:19]([C:23]([OH:28])=[O:24])=[C:20]([Cl:22])[N:21]=2)=[O:15])[CH:10]=[CH:11][CH:12]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 86671248HCID 86671248, compound

Product 1

HCID 86671247HCID 86671247, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 2-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-N-(4-chloro-5-formyl-thiazol-2-yl)-acetamide (590 mg, 1.436 mmol) in t-butanol (15 mL) stirred at 60° C. was added drop wise potassium permanganate (405 mg, 2.56 mmol) in water (5 mL) over 15 minutes. The resultant reaction mixture was heated at 80′C for 2 h. The reaction mixture was filtered hot through celite and washed with hot 1/1 t-butanol/water. The filtrate was acidified to pH 1 with aqueous 2N HCl and extracted with 9:1 Methylene chloride/methanol (3×75 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, filtered, concentrated under reduced pressure and dried to give 2-{2-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acetylamino}-4-chloro-thiazole-5-carboxylic acid (0.52 g, 84.8%) as a pale yellow solid. MS m/e 428.0 (M+H+).

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas heated at 80′C for 2 h
  3. filtrationThe reaction mixture was filtered hot through celite
  4. washwashed with hot 1/1 t-butanol/water
  5. extractionextracted with 9:1 Methylene chloride/methanol (3×75 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customdried

Sources & evidence

ORD record
ord-aafcfcf2da8a41b6906d8b5dda9bc894
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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