(S)-1-(2-Fluorophenyl)ethylamine → HCID 178497675, compound

HRID 339920Notes

Reaction equation

HRID 339920 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[C:15]([CH3:17])([CH3:16])[O:14][C:13](OC)=[N:12][S:11]2(=[O:21])=[O:20])[CH:5]=1.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@@H:30]([NH2:32])[CH3:31]>ClCCl>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[C:15]([CH3:17])([CH3:16])[O:14][C:13]([NH:32][C@H:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[F:23])[CH3:31])=[N:12][S:11]2(=[O:21])=[O:20])[CH:5]=1

Participants

4

Reactant 2

HCID 7023579(S)-1-(2-Fluorophenyl)ethylamineHCID 68359291HCID 68359291, compound

Product 1

HCID 178497675HCID 178497675, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-methoxy-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-5-yl)benzoic acid methyl ester (1.3 g) and (S)-1-(2-fluorophenyl)ethylamine (713 mg) in dichloromethane (15 ml) was stirred under an argon stream and thus concentrated. The residue was left to stand for 4 h, dissolved in ethyl acetate, washed with 1 M HCl and sodium bicarbonate solution, dried over magnesium sulfate and concentrated. This was followed by purification by column chromatography (ethyl acetate/heptane). This gave the product (1.2 g) with a molecular weight of 434.5 g/mol (C21H23FN2O5S).

Workup

  1. concentrationthus concentrated
  2. waitThe residue was left
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with 1 M HCl and sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThis was followed by purification by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-3e98b88e16374b76984a1a22b98a877d
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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