Hydrochloric Acid → 17alpha-Chloroacetoxy-pregn-4-ene-3,20-dione

HRID 1447579

反応式

HRID 1447579 の反応式
F[C:2](F)(F)[C:3]([O:5]C(=O)C(F)(F)F)=O.[OH:14][C@:15]1([C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:25](=[CH:26][C:27](=[O:37])[CH2:28][CH2:29]2)[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[C:16](=[O:18])[CH3:17].C1(C)C=CC=CC=1.[ClH:45]>CO>[Cl:45][CH2:2][C:3]([O:14][C@:15]1([C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:25](=[CH:26][C:27](=[O:37])[CH2:28][CH2:29]2)[CH2:24][CH2:23]3)[CH2:20][CH2:19]1)[C:16](=[O:18])[CH3:17])=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 623817-HydroxyprogesteroneHCID 9845Trifluoroacetic anhydride

生成物 1

HCID 8673671717alpha-Chloroacetoxy-pregn-4-ene-3,20-dione

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of 3-/N,N-bis(2-chloroethyl)amino/-4-methylbenzoic acid (27.6 g) and trifluoroacetic anhydride (21.0 g) is heated under stirring at 60° C. for 15 min. To the mixture 17α-hydroxypregn-4-ene-3,20-dione (16.5 g) is added and the mixture is heated under stirring at 80° C. for 5 h. Toluene (150 ml) is added, the solution is filtered, and to the filtrate chloroform (200 ml) is added. After washing with H2O and aq. NaHCO3, drying, and evaporation an oil is obtained, to which a mixture of methanol (300 ml) and conc. HCl (3 ml) is added. After 16 h at room temperature the solution is evaporated and the residue chromatographed on a silica gel column using toluene/ethyl acetate (2:1) as eluent. The eluate fraction having Rf =0.40 gives 17α-/3-(N,N-bis(2-chloroethyl)amino)-4-methylbenzoyloxy/pregn-4-ene-3,20-dione (1, 6.8 g, m.p. 170°-1° C.).

後処理

  1. temperatureis heated
  2. temperaturethe mixture is heated
  3. stirringunder stirring at 80° C. for 5 h
  4. filtrationthe solution is filtered
  5. additionto the filtrate chloroform (200 ml) is added
  6. washAfter washing with H2O and aq. NaHCO3
  7. customdrying
  8. customevaporation an oil
  9. customis obtained, to which
  10. additionis added
  11. customAfter 16 h at room temperature the solution is evaporated
  12. customthe residue chromatographed on a silica gel column

出典と根拠

ORDレコード
ord-72c0cc4976964636a99400b0f198c648
出典データセット
uspto-grants-1979_12
特許番号
US04177269

関連ノート

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