Acetic Acid → N-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide

HRID 1440

反応式

HRID 1440 の反応式
[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[C:14](=[O:17])[CH2:15][Cl:16])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[C:22](O)(=[O:24])[CH3:23]>O1CCCC1>[C:1]([NH:5][S:6]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[CH:14]([O:17][C:22](=[O:24])[CH3:23])[CH2:15][Cl:16])(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 19690766N-t-butyl-3-chloroacetyl-2-thiophenesulfonamide

生成物 1

HCID 19690764N-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1.5 g (0.005 mole) of N-t-butyl-3-(chloroacetyl)-2-thiophenesulfonamide synthesized in Example 6 was dissolved in the combined solution of 1 ml of acetic acid and 10 ml of tetrahydrofuran and then 0.31 g (0.005 mole) of sodium cyanoborohydride was added slowly thereto. The reaction solution was stirred at normal temperature for 30 minutes and then subjected to a vacuum evaporator to remove the solvent. To the residue was added 10 ml of water and then the resulting solution was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and filtered. To the filtrate were added acetic anhydride, pyridine and N,N-dimethylaminopyridine and the mixture was stirred at normal temperature for 24 hours and then washed with 5% aqueous hydrochloric acid solution. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and the residue was subjected to column chromatography on silica gel to obtain 5 g (Yield: 84%) of the title compound. 1H NMR(CDCl3, δ): 1.3(s, 9H), 2.15(s, 3H), 3.57-3.9(m, 2H), 5.23(s, 1H), 6.5(m, 1H), 7.13(d, 1H), 7.5 (d, 1H)

後処理

  1. customsubjected to a vacuum evaporator
  2. customto remove the solvent
  3. additionTo the residue was added 10 ml of water
  4. extractionthe resulting solution was extracted with methylene chloride
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. additionTo the filtrate were added acetic anhydride, pyridine and N,N-dimethylaminopyridine
  8. stirringthe mixture was stirred at normal temperature for 24 hours
  9. washwashed with 5% aqueous hydrochloric acid solution
  10. customThe organic layer was separated
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-c101707cc7784ad6a6ce1b59640d7a42
出典データセット
uspto-grants-1998_03
特許番号
US05726127

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