Formaldehyde → HCID 10408174、化合物

HRID 2245783ノート

反応式

HRID 2245783 の反応式
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.C=O.[C:29]([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH3:29])=[CH:12][CH:11]=1

参加物

7

反応物 4

HCID 712FormaldehydeHCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11777044Hexanoic acid, 6-[(4-aminophenyl)thio]-, methyl ester

生成物 1

HCID 10408174HCID 10408174、化合物

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒3 回

実験手順

To a solution of 6-(4-amino-phenylsulfanyl)-hexanoic acid methyl ester (1.5 g, 5.9 mmol) in methanol (60 mL) was added a solution of 4-chlorobenzaldehyde (834 mg, 5.9 mmol) in methanol (10 mL). After 1 hour of stirring at room temperature, the solution was cooled at 0° C. and a 37% aqueous solution of formaldehyde (1.44 g, 17.8 mmol) was added. A solution of sodium cyanoborohydride (1.49 g, 23.7 mmol) and zinc chloride (11.9 mmol) in methanol (60 mL) was added in a dropwise. The resulting mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and aqueous sodium hydroxide (75 mL, 2M). The organic layer was washed consecutively with aqueous sodium hydroxide (75 mL, 2M), distilled water (2×75 mL) and brine (75 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an yellow oil that was purified by flash chromatography (5:95:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine). The title compound was obtained as a colourless oil (2.2 g, 83%).

後処理

  1. temperaturethe solution was cooled at 0° C.
  2. stirringThe resulting mixture was stirred at room temperature for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. washThe organic layer was washed consecutively with aqueous sodium hydroxide (75 mL, 2M)
  5. distillationdistilled water (2×75 mL) and brine (75 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an yellow oil that
  10. customwas purified by flash chromatography (5:95:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine)

出典と根拠

ORDレコード
ord-ef80bfb3e9d14a969dce58ecc98aee32
出典データセット
uspto-grants-2010_03
特許番号
US07683185B2

反応ノート

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