Ammonia → HCID 70626912、化合物

HRID 616347ノート

反応式

HRID 616347 の反応式
[FH:1].[C:2]([O:5][C@:6]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C:23](=[CH:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:7](=[O:9])[CH3:8])(=[O:4])[CH3:3].[Br:29]N1C(=O)CCC1=O.N>O.CN(C)C=O>[C:2]([O:5][C@:6]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@:23]([Br:29])([C@@H:24]([F:1])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:7](=[O:9])[CH3:8])(=[O:4])[CH3:3]

参加物

7

反応物 4

HCID 222AmmoniaHCID 14917Hydrofluoric AcidHCID 67184N-bromobutanimideHCID 10762617-Hydroxypregna-4,9(11)-diene-3,20-dione 17-acetate

生成物 1

HCID 70626912HCID 70626912、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

At -78° C., 20 ml. of hydrogen fluoride is combined with 8 ml. of dimethylformamide, and 6 g. of 17-acetoxy-4,9(11)-pregnadiene-3,20-dione (J. Org. Chem. 26 1961!: 866) and 4 g. of N-bromosuccinimide are added to the reaction mixture. The latter is allowed to stand for 3 hours at -30° C. and then introduced into a mixture of water, ice, and a 25% ammonia solution. The precipitate is filtered off, washed with water, taken up in ethyl acetate, and dried over sodium sulfate. After chromatography of the crude product on silica gel with 19-21.6% acetone/hexane, the yield is 3.0 g. of 17-acetoxy- 9-bromo-11β -fluoro-4-pregnene-3,20-dione; m.p. 180°-182° C. (under decomposition).

後処理

  1. customAt -78° C.
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-62706be1eec24027b8b0a08515d82635
出典データセット
uspto-grants-1978_02
特許番号
US04073900

反応ノート

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