Triethylamine → 2,2-dichloro-N-[(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-(4-iodophenyl)ethyl]acetamide

HRID 1500276Notes

Reaction equation

HRID 1500276 reaction equation
[NH2:1][C@H:2]([CH2:12][F:13])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)[OH:4].C(N(CC)CC)C.C([O:23][C:24](=O)[CH:25]([Cl:27])[Cl:26])C>CO>[Cl:26][CH:25]([Cl:27])[C:24]([NH:1][C@H:2]([CH2:12][F:13])[C@H:3]([OH:4])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10808Ethyl dichloroacetateHCID 45257860(2S,1R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol

Product 1

HCID 683504732,2-dichloro-N-[(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-(4-iodophenyl)ethyl]acetamideYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of commercially available (1R,2S)-2-amino-3-fluoro-1-(4-iodophenyl)propan-1-ol (5.0 g, 20.0 mmol) in methanol (100 mL) is added triethylamine (9.56 mL, 67.8 mmol) and ethyldichloroacetate (6.22 mL, 50.8 mmol) and the mixture heated to reflux for 16 hours. After allowing to cool to room temperature, the solvent is removed under reduced pressure and the resultant oil purified by column chromatography eluting from neat heptanes to 80% ethylacetate/heptanes to give the title compound (5.94 g). m/z (Cl) M+H 405.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 16 hours
  3. customthe solvent is removed under reduced pressure
  4. customthe resultant oil purified by column chromatography
  5. washeluting from neat heptanes to 80% ethylacetate/heptanes

Sources & evidence

ORD record
ord-3702796be044452e989ab140af28e0ff
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

Loading…