Hydrochloric Acid → N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

HRID 1451404ノート

反応式

HRID 1451404 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[S:4][CH:5]=[C:6]([C:8](=[O:11])[CH:9]=O)[N:7]=1.[C:14]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([CH3:28])[NH2:27])=[CH:21][CH:20]=1)([O:16][CH2:17]C)=[O:15].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>>[C:14]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH:27][CH2:9][CH:8]([OH:11])[C:6]2[N:7]=[C:3]([C:2]([F:1])([F:12])[F:13])[S:4][CH:5]=2)[CH3:28])=[CH:21][CH:20]=1)([O:16][CH3:17])=[O:15]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 19974143Ethyl 4-(2-aminopropyl)benzoateHCID 199742732-(2-Trifluoromethyl-thiazol-4-yl)glyoxal

生成物 1

HCID 19974173N-[2-(4-Carbomethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

実験手順

1.3 g (0.0062 mol) of 2-(2-trifluoromethyl-thiazol-4-yl)glyoxal and 1.2 g (0.0057 mol) of 2-(4-carboethoxy-phenyl)-1-methyl-ethanamine are mixed at 50° C. and stirred at room temperature for 4 hours. For the reduction of the resulting Schiff's base, 0.75 g of sodium borohydride is added in portions at 20° C., and the mixture is stirred for 16 hours. It is then poured onto ice, and the mixture is acidified with hydrochloric acid, 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 methylene chloride/methanol=40:1 as eluant.

後処理

  1. stirringthe mixture is stirred for 16 hours
  2. additionIt is then poured onto ice
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract is dried over sodium sulphate
  5. concentrationconcentrated
  6. custompurified on a silica gel column

出典と根拠

ORDレコード
ord-27bed3711835414dbfdcc1819f31145c
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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