Toluene → HCID 11624809, compound

HRID 2222898Notes

Reaction equation

HRID 2222898 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].C1(C)C=CC=CC=1.[CH3:31][S-:32].[Na+]>C(OCC)(=O)C>[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:32][CH3:31])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 4378561Sodium methanethiolateHCID 9967675HCID 9967675, compound

Product 1

HCID 11624809HCID 11624809, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

trans-N-Cyanomethyl-2-(4-fluorobenzenesulfonylmethyl)-cyclohexanecarboxamide (102 mg) was weighed into a 2.5 mL vial fitted with a stir vane and nitrogen inlet. Anhydrous toluene (1.5 mL) was added, followed by addition of sodium thiomethoxide (22 mg). The reaction mixture was heated to 70° C. and stirred overnight. After cooling to room temperature, the reaction mixture was stirred for two days. The reaction mixture was diluted with ethyl acetate (15 mL), washed with water and brine. The organic layer was removed, dried over magnesium sulfate and concentrated on a rotary evaporator. Chromatography of the crude product on C-18 reverse-phase HPLC provided the title compound as a white solid.

Workup

  1. customvial fitted with a stir vane and nitrogen inlet
  2. temperatureAfter cooling to room temperature
  3. stirringthe reaction mixture was stirred for two days
  4. washwashed with water and brine
  5. customThe organic layer was removed
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-30d5f391b4c14d3cb4796d3ecf659137
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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