(1S,2R)-(+)-Norephedrine → (1s,2r)-2-{[4-Chloro-6-(3,4-methylenedioxy-phenylamino)-[1,3,5]triazin-2-yl]-amino}-1-phenyl-propan-1-ol

HRID 969272

反応式

HRID 969272 の反応式
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH2:10]1[O:19][C:18]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=2[O:11]1.C(N(C(C)C)CC)(C)C.[CH3:29][CH:30]([NH2:39])[CH:31]([OH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C>[Cl:3][C:2]1[N:1]=[C:8]([NH:15][C:14]2[CH:16]=[CH:17][C:18]3[O:19][CH2:10][O:11][C:12]=3[CH:13]=2)[N:7]=[C:5]([NH:39][C@H:30]([CH3:29])[C@H:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[OH:38])[N:4]=1

参加物

6

反応物 4

HCID 4786(1S,2R)-(+)-NorephedrineHCID 7954Cyanuric chlorideHCID 81531Diisopropylethylamine2 回HCID 843101,3-Benzodioxol-5-amine

生成物 1

HCID 9952786(1s,2r)-2-{[4-Chloro-6-(3,4-methylenedioxy-phenylamino)-[1,3,5]triazin-2-yl]-amino}-1-phenyl-propan-1-ol収率 80%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒5 回

実験手順

To a solution of cyanuric chloride (1.84 gr) in acetonitrile (20 ml), kept at a temperature of −20° C. under stirring, dropwise were subsequently added solutions of 3,4-methylenedioxy-aniline (1.37 gr) in acetonitrile (20 ml) and diisopropylethylamine (DIPEA) (1.29 gr) in acetonitrile (20 ml). After stirring at −20° C. for 1 hour, again dropwise were subsequently added solutions of DIPEA (1.29 gr) in acetonitrile (20 ml) and (1 S,2R)-(+)-norephedrine (1.51 gr) in acetonitrile (20 ml). The mixture was allowed to warm to room temperature and was stirred for another 2 hours. The resulting reaction mixture was concentrated in vacuo. After addition of ethylacetate (250 ml) the organic layer was subsequently washed with a solution of HCl in water (1M, 100 ml), a solution of NaOH in water (1 M, 100 ml) and brine (50 ml). The organic layer was dried over sodiumsulphate, filtered and concentrated in vacuo. The resulting product was purified by column chromatography using silicagel and a mixture of heptane: ethylacetate (3:1) as the eluent. The resulting pure product (formula (9), see above, example B-44, see table) was obtained as a white solid in 80% yield.

後処理

  1. customkept at a temperature of −20° C.
  2. stirringAfter stirring at −20° C. for 1 hour
  3. stirringwas stirred for another 2 hours
  4. customThe resulting reaction mixture
  5. concentrationwas concentrated in vacuo
  6. additionAfter addition of ethylacetate (250 ml) the organic layer
  7. washwas subsequently washed with a solution of HCl in water (1M, 100 ml)
  8. dry with materialThe organic layer was dried over sodiumsulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting product was purified by column chromatography
  12. additiona mixture of heptane: ethylacetate (3:1) as the eluent

出典と根拠

ORDレコード
ord-228629688ad94b00b235bf206514ff28
出典データセット
uspto-grants-2007_12
特許番号
US07307079B2

関連ノート

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