Tetrahydrofuran → ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propoxyimino]acetate

HRID 1649756ノート

反応式

HRID 1649756 の反応式
Cl.Br[CH2:3][CH2:4][CH2:5][NH2:6].[CH2:7](N(CC)CC)C.[NH2:14][C:15]1[S:16][CH:17]=[C:18](/[C:20](=[N:26]/[OH:27])/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=1.[C:28](=[O:31])([O-])[O-:29].[K+].[K+].O1[CH2:38][CH2:37][CH2:36]C1>O.CS(C)=O>[NH2:14][C:15]1[S:16][CH:17]=[C:18](/[C:20](=[N:26]/[O:27][CH2:3][CH2:4][CH2:5][NH:6][C:28]([O:29][C:37]([CH3:36])([CH3:38])[CH3:7])=[O:31])/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=1

参加物

8

反応物 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetateHCID 128607653-Bromopropan-1-amine--hydrogen chloride (1/1)

生成物 1

HCID 88475739ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propoxyimino]acetate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

In a mixture of 100 ml of water and 100 ml of tetrahydrofuran are dissolved 8.76 g of 3-bromopropylamine hydrochloride and 6.72 ml of triethylamine. After addition of 8.73 g of di-tert-butyl bicarbonate, the mixture is stirred at room temperature for 16 hours. The reaction mixture is extracted with ethyl acetate, and the extract is washed with water, 5% aqueous citric acid solution and aqueous sodium chloride solution in that order and then dried over magnesium sulfate. The solvent is then distilled off under reduced pressure to give a light yellow oil. This is dissolved in 80 ml of dimethyl sulfoxide. To the solution are added 8.12 g of ethyl 2-(2-aminothiazol-4-yl)-(Z)-2-hydroxyiminoacetate and 16.56. g of potassium carbonate, and the mixture is stirred at 60° C. for 5 hours. After cooling, the reaction mixture is poured into 800 ml of ice-water and extracted with dichloromethane. The extract is washed with aqueous potassium carbonate solution and aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel (250 g) column chromatography, elution being carried out with hexane-ethylacetate (2:3). The fractions rich in the desired compound are collected and concentrated under reduced pressure to give 5.27 g of ethyl 2-(2-aminothiazol-4-yl)-(Z)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetate as a yellow foamy product.

後処理

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. washthe extract is washed with water, 5% aqueous citric acid solution and aqueous sodium chloride solution in that order
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. customto give a light yellow oil
  6. temperatureAfter cooling
  7. extractionextracted with dichloromethane
  8. washThe extract is washed with aqueous potassium carbonate solution and aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washThe residue is subjected to silica gel (250 g) column chromatography, elution
  12. customThe fractions rich in the desired compound are collected
  13. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-58128795bd434d818a336709cb32a70b
出典データセット
uspto-grants-1990_05
特許番号
US04921851

反応ノート

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