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

HRID 2042926노트

반응식

HRID 2042926 반응식
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]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178506590HCID 178506590, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-08bd0cdb854141ca9fb604c79b258954
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586550B2

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