Sodium Hydroxide → HCID 53248042、化合物

HRID 593271ノート

反応式

HRID 593271 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].N1C=CC=CC=1SSC1C=CC=CN=1.[S:29](Cl)(=[O:32])(=[O:31])[OH:30].[OH-].[Na+]>ClCCCl.CCOC(C)=O.CCCCCC>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][CH:11]([S:29]([OH:32])(=[O:31])=[O:30])[C:12]([OH:14])=[O:13]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acid4 回HCID 650932,2'-Dipyridyl disulfideHCID 116299904-(2-Pyridyldithio)butanoic acid

生成物 1

HCID 53248042HCID 53248042、化合物収率 30.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
75 °C

実験手順

To a solution of 4-(pyridin-2-yldisulfanyl)butanoic acid (725 mg, 3.16 mmol) and 1,2-di(pyridin-2-yl)disulfane (700 mg, 3.18 mmol) in 15 ml of DCE (1,2-dichloroethane) at 75° C. was added chlorosulfuric acid (300 μL, 4.51 mmol). After stirring for 20 min at 75° C., another portion of chlorosulfuric acid (300 μL, 4.51 mmol) was added. The mixture was allowed to stir at 75° C. for 20 min, then another portion of chlorosulfuric acid (200 μL, 3.0 mmol) was added. Again 25 min later, the final portion of chlorosulfuric acid (200 μL, 3.0 mmol) was added and the mixture was stirred for further 25 min. The mixture was immediately cooled on ice bath, neutralized with 1M NaOH to pH ˜7, diluted with EtOAc/Hexane (1:1), separated, and the organic layer was washed with pure water (3×25 ml) while the generated each of aqueous layer was washed with EtOAc/Hexane (1:1, 35 ml). The aqueous layers were combined, acidified with HCl/HOAc to pH 3˜4, concentrated to ˜10 ml, diluted with MeCN (100 ml), sonicated (or quickly stirred) for 1 h, filtered, and the resulting pellet washed with water/MeCN (1:10). The solution was then concentrated and purified on a Si02 cartridge (40 g) eluting with water/MeCN/HOAc (1:10:0.01). To the pooled fractions containing the product, DMF (˜5 ml) was added and evaporated to dryness to afford 4-(pyridin-2-yldisulfanyl)-2-sulfobutanoic acid (295 mg, 0.954 mmol, 30.2% yield).

後処理

  1. stirringto stir at 75° C. for 20 min
  2. stirringthe mixture was stirred for further 25 min
  3. temperatureThe mixture was immediately cooled on ice bath
  4. customseparated
  5. washthe organic layer was washed with pure water (3×25 ml) while the
  6. washwas washed with EtOAc/Hexane (1:1, 35 ml)
  7. concentrationconcentrated to ˜10 ml
  8. additiondiluted with MeCN (100 ml)
  9. customsonicated (or
  10. stirringquickly stirred) for 1 h
  11. filtrationfiltered
  12. washthe resulting pellet washed with water/MeCN (1:10)
  13. concentrationThe solution was then concentrated
  14. custompurified on a Si02 cartridge (40 g)
  15. washeluting with water/MeCN/HOAc (1:10:0.01)
  16. additionTo the pooled fractions containing the product, DMF (˜5 ml)
  17. additionwas added
  18. customevaporated to dryness

出典と根拠

ORDレコード
ord-b9e58159a3e84e018de8f478ea3db0d9
出典データセット
uspto-grants-2016_01
特許番号
US09242936B2

反応ノート

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