Ammonia → HCID 70626912, 화합물

HRID 616347노트

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HRID 616347 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 70626912HCID 70626912, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-62706be1eec24027b8b0a08515d82635
출처 데이터셋
uspto-grants-1978_02
특허 번호
US04073900

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