Ethyl dichloroacetate → HCID 86300700, compound

HRID 1484416Notes

Reaction equation

HRID 1484416 reaction equation
[NH2:1][C@H:2]([CH2:15][F:16])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[NH:13])=[O:12])=[CH:7][CH:6]=1)[OH:4].C([O:19][C:20](=O)[CH:21]([Cl:23])[Cl:22])C>>[Cl:22][CH:21]([Cl:23])[C:20]([NH:1][C@H:2]([CH2:15][F:16])[C@H:3]([OH:4])[C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH3:14])(=[NH:13])=[O:12])=[CH:9][CH:10]=1)=[O:19]

Participants

3

Reactant 2

HCID 10808Ethyl dichloroacetateHCID 117662125HCID 117662125, compound

Product 1

HCID 86300700HCID 86300700, compoundYield 36.4%

Procedure

To a solution of (1R,2S)-2-amino-3-fluoro-1-(4-(S-methylsulfonimidoyl)phenyl)propan-1-ol (76 mg, 0.308 mmol) Methanol (5 mL) is added TEA (0.047 mL, 0.462 mmol) followed by addition of ethyldichloroacetate (0.048 mL, 0.308 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 0.6% MeOH in DCM as an eluent to get 40 mg of the compound which is re-purified by prep HPLC to afford title compound (25 mg) white solid. 1H-NMR (400 MHz, DMSO) δ: 3.0 (s, 3H), 4.19-4.25 (m, 2H), 4.28-4.32 (m, 0.5H), 4.40-4.44 (m, 0.5H), 4.56-4.59 (m, 0.5H), 4.67-4.71 (m, 0.5H), 4.96 (bs, 1H), 6.12 (d, 1H, J=3.6 Hz), 6.47 (d, 1H, J=1.88 Hz), 7.56 (d, 2H, J=8.28 Hz), 7.54 (d, 2H, J=8.28 Hz), 8.82 (d, 1H, J=8.28 Hz). LC-MS (m/z): M+H=357.0.

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-99b7c61717cc4ca09b86200b3dbb24d8
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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