2-Furanmethanethiol → (S)-3-tert-butoxycarbonylamino-1-furfurylthio-2-heptanone

HRID 21576

反応式

HRID 21576 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[C:10](=[O:13])[CH2:11]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([SH:24])[C:19]1[O:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>O1CCCC1.[OH-].[Na+]>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[C:10](=[O:13])[CH2:11][S:24][CH2:18][C:19]1[O:23][CH:22]=[CH:21][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 73632-FuranmethanethiolHCID 516892Sodium BicarbonateHCID 15287852(s)-3-Tert-butoxycarbonylamino-1-chloro-2-heptanone

生成物 1

HCID 15287853(S)-3-tert-butoxycarbonylamino-1-furfurylthio-2-heptanone

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

6.54 g of (S)-3-tert-butoxycarbonylamino-l-chloro-2-heptanone and 3.11 g of furfuryl mercaptan were dissolved in 200 ml of tetrahydrofuran, to which 13 ml solution of 2N sodium hydroxide was added. The reaction solution was stirred at a room temperature for 17 hours and a sodium hydrogencarbonate solution was then added thereto. The solution was extracted with ethyl acetate. The extracted solution was washed with a saturated sodium chloride solution and dried over magnesium sulfate, which was then filtered, concentrated and purified by the silica gel column chromatography (eluent: 10% ethyl acetate containing hexane). The object of 7.82 g was obtained.

後処理

  1. additionwas added
  2. extractionThe solution was extracted with ethyl acetate
  3. washThe extracted solution was washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate, which
  5. filtrationwas then filtered
  6. concentrationconcentrated
  7. custompurified by the silica gel column chromatography (eluent: 10% ethyl acetate containing hexane)
  8. customThe object of 7.82 g was obtained

出典と根拠

ORDレコード
ord-0f38d77b951e4868be38b9ffb7f61fb5
出典データセット
uspto-grants-1995_06
特許番号
US05424325

関連ノート

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