Water → HCID 9901150, compound

HRID 900679Notes

Reaction equation

HRID 900679 reaction equation
C1CO[CH:20]2[CH:3]([CH2:4][C:5]3[C@H:18]([CH2:19]2)[C@@H:17]2[C@H:8]([C@H:9]4[C@@:13]([CH2:15][C@@H:16]2[F:23])([CH3:14])[C@@H:12]([OH:24])[CH2:11][CH2:10]4)[C@H:7]([CH3:25])[CH:6]=3)[O:2]1.C(O)(=O)C(O)=O.O.C(=O)(O)[O-].[Na+]>CO>[F:23][C@H:16]1[CH2:15][C@@:13]2([CH3:14])[C@@H:9]([CH2:10][CH2:11][C@@H:12]2[OH:24])[C@H:8]2[C@H:17]1[C:18]1[CH2:19][CH2:20][C:3](=[O:2])[CH2:4][C:5]=1[CH2:6][C@H:7]2[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 516892Sodium BicarbonateHCID 86597451HCID 86597451, compound

Product 1

HCID 9901150HCID 9901150, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 170 mg of product (C), obtained under 3a), in 22.5 ml of methanol was stirred with 300 mg of oxalic acid and 3 ml of water for 24 hours at room temperature. Then, it was mixed with sodium bicarbonate solution, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 62.7 mg of pure 11β-fluoro-17β-hydroxy-7α-methyl-estr-5(10)-en-3-one (I″) was obtained. Crystallization from hexane yielded 47.6 mg of compound I″ with a melting point of 169.9° C. ([α]D20=+134.4° (c=0.56% chloroform)).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-d749c4e1442e4c8db7b4590fa219a361
Source dataset
uspto-grants-2008_04
Patent number
US07361645B2

Reaction notes

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