Ethyl dichloroacetate → HCID 117662124, compound

HRID 1484414Notes

Reaction equation

HRID 1484414 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C@H:9]([CH2:28][F:29])[C@@H:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:27])(=[N:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[O:19])=[CH:14][CH:13]=1)[OH:11].C([O:32][C:33](=O)[CH:34]([Cl:36])[Cl:35])C>CO>[Cl:35][CH:34]([Cl:36])[C:33]([NH:8][C@H:9]([CH2:28][F:29])[C@H:10]([OH:11])[C:12]1[CH:13]=[CH:14][C:15]([S:18]([CH3:27])(=[N:20][C:21](=[O:26])[C:22]([F:24])([F:25])[F:23])=[O:19])=[CH:16][CH:17]=1)=[O:32]

Participants

4

Reactant 2

HCID 10808Ethyl dichloroacetateHCID 131736729HCID 131736729, compound

Product 1

HCID 117662124HCID 117662124, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1R,2S)-2-Amino-3-fluoro-1-(4-(methyl-N-(2,2,2-trifluoroacetyl)sulfonimidoyl)phenyl)-propan-1-ol TFA salt (426 mg, 1.479 mmol) in Methanol (5 mL) is added TEA (0.299 mL, 2.95 mmol) followed by addition of ethyldichloroacetate (0.279 mL, 1.775 mmol) The resulting reaction mixture is stirred at room temperature for 16 h. Solvent is evaporated in vacuo to get crude which is purified by combi-flash chromatography using 10.3% MeOH in DCM as an eluent to afford title compound (212 mg) as yellow oil. 1H-NMR (400 MHz, DMSO) δ: 3.02 (s, 3H), 4.19-4.13 (m, 1H), 4.15 (bs, 1H), 4.36-4.41 (m, 1.5H), 4.44-4.56 (m, 1H), 4.66-4.69 (m, 0.5H), 4.93 (t, J=4.56 Hz, 1H), 6.0 (d, J=4.64 Hz, 1H), 7.54 (d, J=8.28 Hz, 2H), 7.87 (d, J=8.36 Hz, 2H), 9.49 (d, J=8.36 Hz, 1H). LC-MS (m/z): M+H=343.1 (fragment).

Workup

  1. customThe resulting reaction mixture
  2. customSolvent is evaporated in vacuo
  3. customto get crude which
  4. customis purified by combi-flash chromatography

Sources & evidence

ORD record
ord-646a3cdeeb0b4dc794e7e718f8910246
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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