Sodium ethanethiolate → HCID 68521253, compound

HRID 732838Notes

Reaction equation

HRID 732838 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21]C)[CH:17]=3)[C:12]=2[O:23][C:24]2[CH:38]=[CH:37][C:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([S-])C.[Na+]>CN(C)C=O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH2:20][CH2:19][C:18]3[CH:17]=[C:16]([OH:21])[CH:15]=[CH:14][C:13]=3[C:12]=2[O:23][C:24]2[CH:38]=[CH:37][C:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:26][CH:25]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 59751428HCID 59751428, compound

Product 1

HCID 68521253HCID 68521253, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round bottom flask place the compound of Example 104 (50 mg, 0.094 mmol), sodium ethanethiolate (88 mg, 1.05 mmol) and dimethylformamide (4 mL) in a round bottom flask, at room temperature. Place the reaction in a 95° C. oil bath and stir it for 4 hours, then cool it to ambient temperature. Quench the room temperature mixture with brine and extract it into ethyl acetate. Wash the combined extracts with brine; then dry (sodium sulfate) and concentrate them in vacuo. Purify the crude material on a Chromatotron (silica gel; 5%-12% MeOH gradient in CH2Cl2) to give 7 mg of the title compound (14%). MS (IS+) nm/e 520 (M+1).

Workup

  1. customat room temperature
  2. customthe reaction in a 95° C. oil bath
  3. customQuench the room temperature mixture with brine
  4. extractionextract it into ethyl acetate
  5. washWash the combined extracts with brine
  6. dry with materialthen dry (sodium sulfate)
  7. concentrationconcentrate them in vacuo
  8. customPurify the crude material on a Chromatotron (silica gel; 5%-12% MeOH gradient in CH2Cl2)

Sources & evidence

ORD record
ord-c0d5e9509e35488ea2c4907cc37b4da5
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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