Hydrogen Sulfide → HCID 178484468, compound

HRID 234151Notes

Reaction equation

HRID 234151 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[C:18]([O:31][CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])[CH:17]=2)=[O:15])[CH3:12])=[O:10])[CH2:5][CH2:4]1)#[N:2].N1C=CC=CC=1.C(N(CC)CC)C.[SH2:53]>C(OCC)(=O)C>[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[C:18]([O:31][CH2:32][C:33]([OH:35])=[O:34])[CH:17]=2)=[O:15])[CH3:12])=[O:10])[CH2:5][CH2:4]1)(=[S:53])[NH2:2]

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 1049PyridineHCID 8471TriethylamineHCID 178484465HCID 178484465, compound

Product 1

HCID 178484468HCID 178484468, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Into the solution of the compound prepared in (a) (655 mg, 1.2 mmole) in the mixture of pyridine (15 ml) and triethylamine (1 ml) was streamed a hydrogen sulfide gas for 1 hour, and the mixture was stirred in a sealed tube at 50° C. for 5 hours. After the reaction mixture was cooled to room temperature, it was diluted with ethyl acetate, and washed twice with each of a 5% aqueous sodium hydrogen carbonate and a 1M potassium hydrogen sulfate solution. After the organic layer was dried over anhydrous magnesium sulfate, the inorganic salt was removed by filtration. The filtrate was concentrated under reduced pressure, and the oily product thus obtained was purified by column chromatography on silica gel with an eluent system of chloroform:methanol =50:1 to give 71 mg of the thioamide derivative as a yellow oily product (yield, 10%).

Workup

  1. customfor 1 hour
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. washwashed twice with each of a 5% aqueous sodium hydrogen carbonate
  4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  5. customthe inorganic salt was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe oily product thus obtained
  8. customwas purified by column chromatography on silica gel with an eluent system of chloroform

Sources & evidence

ORD record
ord-f8ef41cbc844409abf58cde56fc49b0b
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Reaction notes

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