(S)-1-(2-Fluorophenyl)ethylamine → HCID 178462012, compound

HRID 339870Notes

Reaction equation

HRID 339870 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11](OC)=[N:10][S:9]2(=[O:19])=[O:18])[CH:5]=[CH:6][CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C@@H:28]([NH2:30])[CH3:29]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:20])[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:30][C@H:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[F:21])[CH3:29])=[N:10][S:9]2(=[O:19])=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7023579(S)-1-(2-Fluorophenyl)ethylamineHCID 683591715-(3-Bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178462012HCID 178462012, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 209 mg of 5-(3-bromophenyl)-2-methoxy-5,6,6-trimethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 92 mg of (S)-1-(2-fluorophenyl)ethylamine in 5 ml of methylene chloride was stirred at room temperature for 1 hour and the conversion was checked by LCMS. Since no conversion had taken place yet, the solvent was concentrated by rotary evaporation and the residue was stirred at room temperature for 19 hours. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (170 mg) with a molecular weight of 469.4 g/mol (C20H22BrFN2O3S); MS (ESI): m/e=469 (M+H+).

Workup

  1. concentrationthe solvent was concentrated by rotary evaporation
  2. customThe crude product was purified by means of normal phase chromatography
  3. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d90dd1d3fdd44c2e9bf407e0efe1df8a
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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