Ammonium Chloride → tert-Butyl 2-oxo-2-(thiophen-3-yl)ethylcarbamate

HRID 2042926ノート

反応式

HRID 2042926 の反応式
CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[S:16]1[CH:20]=[CH:19][C:18]([Mg]I)=[CH:17]1.[NH4+].[Cl-]>C1COCC1>[O:14]=[C:4]([C:18]1[CH:19]=[CH:20][S:16][CH:17]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178506590HCID 178506590、化合物

生成物 1

HCID 67995722tert-Butyl 2-oxo-2-(thiophen-3-yl)ethylcarbamate収率 46%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the Weinreb amide 45 (1.53 g, 7 mmol) in anhydrous THF (10 mL) was added dropwise (over a 10-min period) a solution of thiophen-3-ylmagnesium iodide (0.3 M in THF, 50 mL) under nitrogen atmosphere at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was poured into a saturated NH4Cl solution and extracted with EtOAc. The organic phase was dried over anhydrous MgSO4, filtered and evaporated under vacuum. The residue was further purified by silica column chromatography to provide the titled compound (776 mg, 46%). MNa+264.

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was further purified by silica column chromatography

出典と根拠

ORDレコード
ord-08bd0cdb854141ca9fb604c79b258954
出典データセット
uspto-grants-2013_11
特許番号
US08586550B2

反応ノート

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