Sodium methanethiolate → HCID 18914198, compound

HRID 128600Notes

Reaction equation

HRID 128600 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:10][CH:9]1[CH2:21][CH2:22]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][S-:29].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:10][CH:9]1[CH2:21][CH2:22][S:29][CH3:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 18914159HCID 18914159, compound

Product 1

HCID 18914198HCID 18914198, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1-t-butyloxycarbonyl-2-(2-methylsulfonyloxyethyl)-4-(2-methylphenyl)piperazine from Step 1 above (0.39 g; 0.98 mmol) and sodium thiomethoxide (0.21 g; 3.0 mmol) in dry THF (15 mL) was heated to reflux for 18 h. The solvent was evaporated under reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was separated and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 1:4 EtOAc:hexanes as eluant. The title compound was isolated as a gum (1H-NMR: consistent with structure; TLC: silica gel, 1:4 EtOAc:hexanes: single component, Rf =0.50; FABMS: M+H @ m/e=351; HPLC: >99%, retention time 12.0 min).

Workup

  1. temperatureto reflux for 18 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-44d513311dcc4b5baf9ea42ebb2cb30f
Source dataset
uspto-grants-1995_11
Patent number
US05464788

Reaction notes

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