Methyl iodide → HCID 178489709, compound

HRID 339858Notes

Reaction equation

HRID 339858 reaction equation
[CH:1]1([NH:7][C:8]2[O:9][C:10]([CH3:24])([CH3:23])[CH:11]([C:16]3[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=3)[S:12](=[O:15])(=[O:14])[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25]C(C)([O-])C.[K+].CI>CN1C(=O)CCC1.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH:1]1([NH:7][C:8]2[O:9][C:10]([CH3:24])([CH3:23])[CH:11]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:25])[CH:17]=3)[S:12](=[O:15])(=[O:14])[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178431655HCID 178431655, compound

Product 1

HCID 178489709HCID 178489709, compoundYield 43.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of 120 mg of 3-(2-cyclohexylamino-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]oxathiazin-5-yl)phenol in 2 ml of NMP were added, at room temperature, 38 mg of potassium tert-butoxide and 97 mg of methyl iodide, and the reaction mixture was stirred at constant temperature for 2.5 hours. The reaction solution was diluted with 60 ml of water, 5 ml of 5% aqueous sodium thiosulfate solution were added, and the mixture was extracted twice with 30 ml of ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation, and the residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fraction was lyophilized. This gave the product (54 mg) with a molecular weight of 366.5 g/mol (C18H26N2O4S); MS (ESI): m/e=367 (M+H+).

Workup

  1. additionwere added
  2. extractionthe mixture was extracted twice with 30 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customthe residue was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-c2c1c3efd02d4311b518937c59f246ab
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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