Potassium Carbonate → HCID 117662125, compound

HRID 1484415Notes

Reaction equation

HRID 1484415 reaction equation
ClC(Cl)C([NH:5][C@H:6]([CH2:25][F:26])[C@H:7]([OH:24])[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:23])(=[N:16]C(=O)C(F)(F)F)=[O:15])=[CH:10][CH:9]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:5][C@H:6]([CH2:25][F:26])[C@@H:7]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH3:23])(=[NH:16])=[O:15])=[CH:12][CH:13]=1)[OH:24]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 117662124HCID 117662124, compound

Product 1

HCID 117662125HCID 117662125, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2, 2-Dichloro-N-[(1S,2R)-1-fluoromethyl-2-hydroxy-2-(4-(methyl-N-(2,2,2-trifluoroacetyl)sulfonimidoyl)phenyl)-ethyl]-acetamide (212 mg, 0.468 mmol) in Methanol (20 mL) is added K2CO3 (322.9 mg, 2.34 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 15% MeOH in DCM as an eluent and washed with n-pentane and diethyl ether to afford title compound (80 mg). 1H-NMR (400 MHz, DMSO) δ: 1.60 (bs, 2H), 3.04 (s, 3H), 4.13-4.15 (m, 1.5H), 4.21-4.42 (m, 0.5H), 4.42-4.31 (m, 0.5H), 4.39-4.43 (m, 0.5H), 4.66 (bs, 1H), 7.55 (d, J=8.28 Hz, 2H), 7.87 (d, J=8.32 Hz, 2H). LC-MS (m/z): M+H=247.2.

Workup

  1. customthe resulting reaction mixture
  2. customSolvent is evaporated in vacuo
  3. customto get crude which
  4. customis purified by combi-flash chromatography
  5. washwashed with n-pentane and diethyl ether

Sources & evidence

ORD record
ord-e1a70078e4224439902e872389fafce7
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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