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

HRID 53453노트

반응식

HRID 53453 반응식
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]

참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 67707009HCID 67707009, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1824a984860b457ebf39dcbc5644275f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618806

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