L-Methionine → HCID 22349427, compound

HRID 896030Notes

Reaction equation

HRID 896030 reaction equation
[CH:1]([N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([O:13][C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)=[CH:10]2)=[N:5]1)([CH3:3])[CH3:2].N[C@H](C(O)=O)CCSC.[OH-].[Na+].C(=O)(O)[O-].[Na+]>CS(O)(=O)=O.O>[CH:1]([N:4]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([O:13][C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)=[CH:10]2)=[N:5]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6137L-MethionineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 22349438HCID 22349438, compound

Product 1

HCID 22349427HCID 22349427, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 2-Isopropyl-5-(4-methoxy-phenoxy)-2H-indazole (0.075 grams, mmol) in 2 mL of methanesulfonic acid was treated with 0.15 grams of methionine. After stirring for 24 hours at room temperature, the mixture was treated with 1.2 grams of sodium hydroxide in 25 mL of water with cooling in an ice bath, neutralized with aqueous sodium bicarbonate, extracted 3 times with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo, affording 0.070 grams of 4-(2-Isopropyl-2H-indazol-5-yloxy)-phenol as a colorless syrup. MS: 269.7 [M+H]+

Workup

  1. temperaturewith cooling in an ice bath
  2. extractionextracted 3 times with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38a3622368af4a8594318bf210a9424d
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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