Acetone → 16-Azido-3-methoxyestra-1(10),2,4-trien-17-one

HRID 1050287ノート

反応式

HRID 1050287 の反応式
[N:1]([C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C@H:5]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+:2]=[N-:3].CC(C)=O.C(O)(C)C>S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[N:1]([C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C:5]1=[O:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+:2]=[N-:3]

参加物

6

反応物 3

HCID 180AcetoneHCID 3776IsopropanolHCID 21723401HCID 21723401、化合物

生成物 1

HCID 16265816-Azido-3-methoxyestra-1(10),2,4-trien-17-one

試薬・触媒・溶媒 2

HCID 10219390chromium (VI) trioxide触媒HCID 1118Sulfuric Acid溶媒

実験手順

To a solution of 20 g 16α-azido-3-methoxy-estra-1,3,5(10)-triene-17β-ol in 11 acetone, 40 ml of 8 N chromium trioxide solution in conc. sulfuric acid is added dropwise at 0° C. and under stirring. After 2 h, 2 ml isopropanol are added and the reaction product is precipitated in crystalline form by dropwise addition of water. The product is filtered off, washed with water, dried and recrystallized from acetone/water. Yield: 16 g (81%), F=118-122° C.; [α]D+405°. IR: 1747 cm (CO), 2095 (N3).

後処理

  1. customthe reaction product is precipitated in crystalline form by dropwise addition of water
  2. filtrationThe product is filtered off
  3. washwashed with water
  4. customdried
  5. customrecrystallized from acetone/water
  6. customYield: 16 g (81%), F=118-122° C.

出典と根拠

ORDレコード
ord-47b6e540f34d4cbba60c0197cc9738c5
出典データセット
uspto-grants-2016_07
特許番号
US09382288B2

反応ノート

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