Potassium Carbonate → HCID 10194921, compound

HRID 2222897Notes

Reaction equation

HRID 2222897 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2].C(=O)([O-])[O-].[K+].[K+].[SH:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C=O>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 9967675HCID 9967675, compound

Product 1

HCID 10194921HCID 10194921, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

trans-N-Cyanomethyl-2-(4-fluorobenzenesulfonylmethyl)cyclohexanecarboxamide (3.384 g, 10 mmol) and potassium carbonate (2.34 g, 17 mmol) were weighed into a 100 mL round bottom flask fitted with a stir bar and a cap. Ethyl 2-mercaptoacetate (1.86 mL) was added, followed by the addition of dimethylformamide (30 mL). The reaction vessel was flushed with nitrogen and then sealed with a cap. After stirring the reaction mixture at 100° C. for 2 h, the reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was diluted with ethyl acetate (300 mL), filtered, and washed with brine. The organic layer was dried over magnesium sulfate, filtered and evaporated on a rotavap. The residue was chromatographed on 500 cm3 of silica gel in a 5×25 cm column with 50:50 dichloromethane:ethyl acetate eluent to give the title compound as a white solid. 1H NMR (DMSO-d6): =8.59 (1H, t), 7.69 (2H,dd), 7.49 (2H,dd), 4.44-4.04 (6H, m), 3.37 (1H, q), 2.95 (1H, dd), 2.2-1.8(3H, m), 1.62 (3H, m), 1.30 (1H, m), 1.16 (6H, m) MS [ESI, (M−H)−] m/z=437.2 amu

Workup

  1. customfitted with a stir bar
  2. customThe reaction vessel was flushed with nitrogen
  3. customsealed with a cap
  4. stirringto stir overnight at room temperature
  5. additionThe reaction mixture was diluted with ethyl acetate (300 mL)
  6. filtrationfiltered
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated on a rotavap
  11. customThe residue was chromatographed on 500 cm3 of silica gel in a 5×25 cm column with 50:50 dichloromethane

Sources & evidence

ORD record
ord-3c02c3d3928342d99036e2082d055ff1
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

Loading…