Triethylamine → 21-[4-Carboxy-3-(4-hydroxyphenyl)-1-oxobutoxy]-11beta,18-epoxy-18-hydroxypregn-4-ene-3,20-dione

HRID 67209ノート

反応式

HRID 67209 の反応式
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:41][C:42]([OH:44])=[O:43])[CH2:12][C:13](=[O:40])[O:14][CH2:15][C:16](=[O:39])[C@@H:17]2[C@@:34]34[CH:35]([O:37][C@@H:32]([CH2:33]3)[C@H:31]3[C@@H:21]([CH2:22][CH2:23][C:24]5[C@:29]3([CH3:30])[CH2:28][CH2:27][C:26](=[O:38])[CH:25]=5)[C@@H:20]4[CH2:19][CH2:18]2)[OH:36])=[CH:7][CH:6]=1)(=O)C.C(N(CC)CC)C>CO>[C:42]([CH2:41][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=1)[CH2:12][C:13](=[O:40])[O:14][CH2:15][C:16](=[O:39])[C@@H:17]1[C@@:34]23[CH:35]([O:37][C@@H:32]([CH2:33]2)[C@H:31]2[C@@H:21]([CH2:22][CH2:23][C:24]4[C@:29]2([CH3:30])[CH2:28][CH2:27][C:26](=[O:38])[CH:25]=4)[C@@H:20]3[CH2:19][CH2:18]1)[OH:36])([OH:44])=[O:43]

参加物

4

反応物 2

HCID 8471TriethylamineHCID 7054401921-[3-(4-Acetyloxyphenyl)-4-carboxy-1-oxobutoxy]-11beta,18-epoxy-18-hydroxypregn-4-ene-3,20-dione

生成物 1

HCID 7054183421-[4-Carboxy-3-(4-hydroxyphenyl)-1-oxobutoxy]-11beta,18-epoxy-18-hydroxypregn-4-ene-3,20-dione収率 68.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 21-[3-(4-acetyloxyphenyl)-4-carboxy-1-oxobutoxy]-11β,18-epoxy-18-hydroxypregn-4-ene-3,20-dione (130 mg) in anhydrous methanol (15 ml) containing triethylamine (0.2 ml) is allowed to stand at room temperature for 24 hours. The methanol is then evaporated in vacuo, the residue is diluted with water (5.0 ml), acidified with 10% hydrochloric acid and extracted with ethyl acetate (three 5.0 ml portions). The ethyl acetate solution is washed with brine, dried over anhydrous magnesium sulfate, evaporated and the residue is subjected to preparative thin-layer chromatography on silica gel plates (using chloroform-methanol, 9:1 for development) to isolate 83 mg of the title compound, melting point 145°-152° C., with consistent spectral data.

後処理

  1. customThe methanol is then evaporated in vacuo
  2. additionthe residue is diluted with water (5.0 ml)
  3. extractionextracted with ethyl acetate (three 5.0 ml portions)
  4. washThe ethyl acetate solution is washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-0ed13fb411a7432faa06c3045a297a40
出典データセット
uspto-grants-1982_08
特許番号
US04345096

反応ノート

読み込み中…