1-Phenethylamine, (-)- → HCID 178462014, compound

HRID 2369961Notes

Reaction equation

HRID 2369961 reaction equation
FC1C=CC=C(F)C=1O[C:5]1[O:6][C:7]([CH3:16])([CH3:15])[C:8]([CH3:14])([CH3:13])[S:9](=[O:12])(=[O:11])[N:10]=1.[C:22]1([C@@H:28]([NH2:30])[CH3:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([C@@H:28]([NH:30][C:5]2[O:6][C:7]([CH3:15])([CH3:16])[C:8]([CH3:13])([CH3:14])[S:9](=[O:11])(=[O:12])[N:10]=2)[CH3:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 867054542-(2,6-Difluorophenoxy)-5,5,6,6-tetramethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178462014HCID 178462014, compoundYield 50.9%

Procedure

A mixture of 194 mg of 2-(2,6-difluorophenoxy)-5,5,6,6-tetramethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 737 mg of (S)-1-phenylethylamine was stirred at room temperature for 16 hours and then purified in a purification laboratory by means of preparative HPLC. The combined product-containing fractions were alkalized with 25% aqueous ammonia solution and extracted three times with 30 ml of ethyl acetate, and the combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. This gave the product (96 mg) with a molecular weight of 310.4 g/mol (C15H22N2O3S); MS (ESI): m/e=311 (M+H+).

Workup

  1. custompurified in a purification laboratory by means of preparative HPLC
  2. additionThe combined product-containing fractions
  3. extractionextracted three times with 30 ml of ethyl acetate
  4. dry with materialthe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-cc75699783da45c9935f191b8d71f8ad
Source dataset
uspto-grants-2014_04
Patent number
US08710050B2

Reaction notes

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