Potassium sodium tartarate → N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide

HRID 1654288ノート

反応式

HRID 1654288 の反応式
[CH2:1]([NH:3][C:4](=O)[CH2:5][CH2:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][CH:7]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:12][CH:13]=1)[OH:19])[CH3:2]

参加物

5

反応物 3

HCID 9855836Potassium sodium tartarateHCID 10637817N-ethyl-gamma-oxo-4-((methanesulfonyl)amino)benzenebutanamideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 10779588N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide収率 18.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The product from Step I (3.0 g, 0.010 mol) was added in small portions, under nitrogen to a stirred, ice-cold mixture of LiAlH4 (1.15 g, 0.030 mol) in THF (75 ml). This mixture was kept in the ice bath for 1 hour and at ambient temperature for 2 hours. It was then mixed with an additional 100 ml of THF, refluxed for a few minutes and kept at ambient temperature for 18 hours. The mixture was treated carefully with 69 ml of a saturated sodium potassium tartrate solution and stirred for 1 hour. It was extracted with EtOAc. The extract was washed with a dilute sodium chloride solution. The aqueous layer contained the product; it was concentrated and finally freeze-dried. The resulting solid was extracted with MeOH. The methanol solution was concentrated and the residue extracted with CH2Cl2. The CH2Cl2 solution was concentrated to give 1.6 g of crude product that was purified by chromatography on silica gel with 1% NH4OH-10 to 20% MeOH--CHCl3. The product was crystallized from MeOH--EtOAc to give 540 mg of N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide, mp 174°-176° C. The analytical sample was crystallized from MeOH and had mp 178.5°-180.5° C. Anal. calc'd for C13H22N2O3S: C, 54.52; H, 7.74; N, 9.78; S, 11.20. Found: C, 54.40; H, 7.84; N, 10.00; S, 11.02.

後処理

  1. temperaturerefluxed for a few minutes
  2. extractionIt was extracted with EtOAc
  3. washThe extract was washed with a dilute sodium chloride solution
  4. concentrationit was concentrated
  5. customfinally freeze-dried
  6. extractionThe resulting solid was extracted with MeOH
  7. concentrationThe methanol solution was concentrated
  8. extractionthe residue extracted with CH2Cl2
  9. concentrationThe CH2Cl2 solution was concentrated
  10. customto give 1.6 g of crude product that
  11. customwas purified by chromatography on silica gel with 1% NH4OH-10 to 20% MeOH
  12. customThe product was crystallized from MeOH

出典と根拠

ORDレコード
ord-fdd611fa6322449d95de17ad1db421da
出典データセット
uspto-grants-1995_04
特許番号
US05405997

反応ノート

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