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

HRID 53453Notes

Reaction equation

HRID 53453 reaction equation
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]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 67707009HCID 67707009, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1824a984860b457ebf39dcbc5644275f
Source dataset
uspto-grants-1997_04
Patent number
US05618806

Reaction notes

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