Methanol → 17beta-[3-(4-Carboxyphenyl)propionyl]-estra-1,3,5(10)-triene-3-carboxylic acid

HRID 53453ノート

反応式

HRID 53453 の反応式
C[O:2][C:3]([C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([C:23](=[O:35])[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=3)[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].CO>O>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][C:23]([C@H:14]2[CH2:13][CH2:12][C@H:11]3[C@H:10]4[C@H:19]([CH2:18][CH2:17][C@:15]23[CH3:16])[C:20]2[CH:21]=[CH:22][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH2:8][CH2:9]4)=[O:35])=[CH:31][CH:30]=1)([OH:34])=[O:33]

参加物

5

反応物 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 67707009HCID 67707009、化合物

生成物 1

HCID 5409846817beta-[3-(4-Carboxyphenyl)propionyl]-estra-1,3,5(10)-triene-3-carboxylic acid収率 80%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of methyl-17β-[3-(4-carboxyphenyl)propionyl]-estra-1,3,5(10)-triene-3-carboxylate (0.053 g, 0.11 mmoles), K2CO3 (50 mg, 0.36 mmoles), MeOH (9 ml) and H2O (1 ml) was refluxed under argon. Methanol was evaporated and the residue was acidified with dilute HCl. Extracted with EtOAc. The organic layer was washed with H2O, brine, dried and concentrated. The residue was chromatographed (silica gel) eluting with 1% MeOH in CH2Cl2 containing 1% HOAC to give the title compound as a white solid (40 mg, 80%), mp 285°-290° C.

後処理

  1. temperaturewas refluxed under argon
  2. customMethanol was evaporated
  3. extractionExtracted with EtOAc
  4. washThe organic layer was washed with H2O, brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with 1% MeOH in CH2Cl2 containing 1% HOAC

出典と根拠

ORDレコード
ord-1824a984860b457ebf39dcbc5644275f
出典データセット
uspto-grants-1997_04
特許番号
US05618806

反応ノート

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