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

HRID 904079Notes

Reaction equation

HRID 904079 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bf97a4e84cae49069b0caa1f681b9dc1
Source dataset
uspto-grants-1980_10
Patent number
US04230621

Reaction notes

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