Sodium Iodide → N-(3-Acetylthio-2-methylpropanoyl)-N-cyclopentylglycine

HRID 127627ノート

反応式

HRID 127627 の反応式
C([O:5][C:6](=[O:23])[CH2:7][N:8]([C:14](=[O:22])[CH:15]([CH3:21])[CH2:16][S:17][C:18](=[O:20])[CH3:19])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.C[Si](Cl)(C)C.[I-].[Na+].C(#N)C>O>[C:18]([S:17][CH2:16][CH:15]([CH3:21])[C:14]([N:8]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)[CH2:7][C:6]([OH:23])=[O:5])=[O:22])(=[O:20])[CH3:19]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 13599173HCID 13599173、化合物

生成物 1

HCID 13599174N-(3-Acetylthio-2-methylpropanoyl)-N-cyclopentylglycine収率 90.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

N-(3-Acetylthio-2-methylpropanoyl)-N-cyclopentylglycine t-butyl ester (80.1 g, 0.23 mol), trimethylsilyl chloride (37.9 g, 0.35 mol), and sodium iodide (52.5 g, 0.35 mol) were added to acetonitrile (300 ml), and the reaction mixture was stirred at 45° C.-50° C. for 30 minutes. Water (50 ml) was then added and the mixture was concentrated. The residue was dissolved in saturated aqueous sodium bicarbonate (400 ml) and was washed with ethyl acetate (3×400 ml). The aqueous portion was separated, acidified (conc. hydrochloric acid), and extracted with ethyl acetate. The organic extracts were combined, dried over Na2SO4 and MgSO4, filtered and concentrated yielding the crude desired product as a brown oil (60 g, 90%). When this material was eluted through a high pressure liquid chromatography column with ethyl acetate/hexane/acetic acid (60:40:2) a slightly yellow oil was obtained. This compound was characterized as its DCHA salt which was prepared by adjusting to pH 9 an acetonitrile solution of the compound with DCHA. The salt was obtained as a white crystalline solid, m.p, 172°-174° C.

後処理

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in saturated aqueous sodium bicarbonate (400 ml)
  3. washwas washed with ethyl acetate (3×400 ml)
  4. customThe aqueous portion was separated
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over Na2SO4 and MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-9fb7f97cb57042399fd4b8dfde950160
出典データセット
uspto-grants-1981_03
特許番号
US04256761

反応ノート

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