Benzoyl chloride → HCID 54333087, compound

HRID 486741Notes

Reaction equation

HRID 486741 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][S:9][C@@H:8]([CH2:11][SH:12])[CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([S:12][CH2:11][C@H:8]1[CH2:7][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][S:9]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 53870179HCID 53870179, compound

Product 1

HCID 54333087HCID 54333087, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of trans-4-ethoxycarbonyl-2-mercaptomethyltetrahydrothiophene (compound No. 15-1, 60 mg) and triethylamine (42 μl) in methylene chloride (2 ml), benzoyl chloride (43 mg) dissolved in methylene chloride (1 ml) was added under ice-cooling. The mixture was stirred for 10 minutes and concentrated in vacuo. 0.1N hydrochloric acid was added to the residue and extracted with diethylether. The organic layer was washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 77 mg (86%) of the titled compound (compound No. 23-1).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. concentrationconcentrated in vacuo
  4. addition0.1N hydrochloric acid was added to the residue
  5. extractionextracted with diethylether
  6. washThe organic layer was washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-2c160ce0db124aec89085c2f699ec324
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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