Dimethyl Sulfide → Methyl 4-[2-(thiazol-2-ylamino)ethyloxy]benzoate

HRID 583693ノート

反応式

HRID 583693 の反応式
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH2:7][C:8]([O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=O.CSC>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][CH2:7][CH2:8][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1

参加物

4

反応物 2

HCID 1068Dimethyl SulfideHCID 18928580Methyl 4-[(thiazol-2-ylamino)acetyloxy]benzoate

生成物 1

HCID 18928557Methyl 4-[2-(thiazol-2-ylamino)ethyloxy]benzoate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Amide 24-3 (1.0 g, 3.4 mmol) was dissolved in 7 mL toluene at 0°, and BH3.DMS (341 μL, 3.6 mmol) was added. After 15 min, the reaction was heated to reflux for 16 h, cooled to 0°, and quenched with 10% Na2CO3. The mixture was extracted with EtOAc, the organic phase was washed with water and brine, dried (MgSO4), concentrated, and purified by flash chromatography (silica, 70% EtOAc/hexane) providing 24-4 as a white solid. Rf 0.64 (silica, EtOAc).

後処理

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 16 h
  3. temperaturecooled to 0°
  4. customquenched with 10% Na2CO3
  5. extractionThe mixture was extracted with EtOAc
  6. washthe organic phase was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by flash chromatography (silica, 70% EtOAc/hexane)

出典と根拠

ORDレコード
ord-23d2597344324be4a5ccd85f6bff66d1
出典データセット
uspto-grants-1999_07
特許番号
US05929120

反応ノート

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