Sodium Methoxide → HCID 21879415, compound

HRID 724602Notes

Reaction equation

HRID 724602 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][S:18]C(=O)C)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C[O-].[Na+]>O1CCCC1.CO>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][SH:18])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 58746591HCID 58746591, compound

Product 1

HCID 21879415HCID 21879415, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.35-A of Step 1 (160 mg, 0.49 mmol) in tetrahydrofuran (1.5 mL) and methanol (1.5 mL) was cooled to 0° C. and degassed. The reaction mixture was treated with sodium methoxide (0.30 mL, 3.3 mmol, 25 wt % solution in methanol) dropwise and stirred at 0° C. for 5 min. The reaction mixture was quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was separated and washed with brine (10 mL), dried with sodium sulfate, filtered, and concentrated to give a white solid which was used in the next step without further purification. LCMS found for C14H15O2S2 (M+H)+: m/z=279.

Workup

  1. customdegassed
  2. customThe reaction mixture was quenched with saturated ammonium chloride (20 mL)
  3. extractionextracted with ethyl acetate (30 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (10 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a white solid which
  10. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-efccdabad8704070b71a35213e5a499c
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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