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

HRID 2283167Notes

Reaction equation

HRID 2283167 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 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 the resultant oil
  4. custompurified by column chromatography
  5. washeluting from neat heptanes to 80% ethylacetate/heptanes

Sources & evidence

ORD record
ord-45c830550d0e4c1fba94fc154b454d2f
Source dataset
uspto-grants-2015_09
Patent number
US09145355B2

Reaction notes

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