Sodium borohydride → HCID 14076215、化合物

HRID 1451398ノート

反応式

HRID 1451398 の反応式
[C:1]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:18])[CH2:16]Br)[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=1)([O:21][CH2:22][CH3:23])=[O:20].[BH4-].[Na+]>C(Cl)Cl.CO.NC(N)=O>[C:19]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][CH2:16][CH:15]([OH:18])[C:13]2[N:14]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:11][CH:12]=2)=[CH:26][CH:25]=1)([O:21][CH2:22][CH3:23])=[O:20]

参加物

7

反応物 3

HCID 4311764Sodium borohydrideHCID 12945884Ethyl 4-(2-aminoethyl)benzoateHCID 14076214HCID 14076214、化合物

生成物 1

HCID 14076215HCID 14076215、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 1176Urea溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

9.6 g (0.03 mol) of 2-Benzoylamino-4-bromoacetyl-thiazole are dissolved in 100 ml of methylene chloride and, while stirring at room temperature, added dropwise to a solution of 11.5 g (0.06 mol) of 2-(4-carboethoxyphenyl)ethylamine in 150 ml of methylene chloride. After 1.5 hours, the mixture is cooled to 5° C., diluted with 200 ml of methanol and, for the reduction of the resulting amino-ketone, 3 g of sodium borohydride are added in small portions at 0°-5° C. After 3 hours the solution is evaporated to dryness, ice/water is added, and hydrochloric acid is used to acidify. After 10 minutes the mixture is made alkaline with sodium bicarbonate solution and extracted with methylene chloride. The extract is dried over sodium sulphate, concentrated and purified on a silica gel column using chloroform/methanol=9:1, with the addition of 2% ammonia-saturated ethanol, as eluant. The resulting product is induced to crystallise with petroleum ether.

後処理

  1. temperaturethe mixture is cooled to 5° C.
  2. additionare added in small portions at 0°-5° C
  3. customAfter 3 hours the solution is evaporated to dryness, ice/water
  4. additionis added
  5. waitAfter 10 minutes the mixture is made
  6. extractionalkaline with sodium bicarbonate solution and extracted with methylene chloride
  7. dry with materialThe extract is dried over sodium sulphate
  8. concentrationconcentrated
  9. custompurified on a silica gel column
  10. additionwith the addition of 2% ammonia-saturated ethanol
  11. customto crystallise with petroleum ether

出典と根拠

ORDレコード
ord-59a3b648a7654c15a6839f397e6f7e41
出典データセット
uspto-grants-1997_02
特許番号
US05604225

反応ノート

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