Hydrochloric Acid → HCID 68130030, compound

HRID 1581066Notes

Reaction equation

HRID 1581066 reaction equation
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:24])[CH2:9][CH2:10][C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[C@@H:14]([OH:23])[CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1.Cl>N1C=CC=CC=1>[C:25]([O:23][C@@H:14]1[C:15]2[C@:21]([CH3:22])([CH2:20][CH2:19][C:17](=[O:18])[CH:16]=2)[C@@H:11]2[C@H:12]([C@H:7]3[C@:8]([CH3:24])([CH2:9][CH2:10]2)[C@@H:4]([C:2](=[O:3])[CH3:1])[CH2:5][CH2:6]3)[CH2:13]1)(=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 23239832HCID 23239832, compound

Product 1

HCID 68130030HCID 68130030, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Two grams of 6α-hydroxyprogesterone is refluxed for 1 hour in 20 ml. of pyridine with 4 g. of succinic acid anhydride. After cooling, the solution is stirred into ice water and acidified with 1N hydrochloric acid. The smeary precipitation product is separated and dissolved in methylene chloride; the solution is washed with hydrochloric acid and water and evaporated under vacuum. The residue (2.57 g. of foam) is dissolved in methanol, combined with carbon, filtered, and the filtrate concentrated under vacuum. By trituration of the residue with pentane, 2.1 g. of amorphous (3,20-dioxo-4-pregnen-6α-yl) hydrogen succinate is produced. UV: ε238 = 14,100.

Workup

  1. temperatureAfter cooling
  2. customThe smeary precipitation product is separated
  3. dissolutiondissolved in methylene chloride
  4. washthe solution is washed with hydrochloric acid and water
  5. customevaporated under vacuum
  6. dissolutionThe residue (2.57 g. of foam) is dissolved in methanol
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-c364ff95b6ad42cfa86deca9567769b6
Source dataset
uspto-grants-1976_01
Patent number
US03935245

Reaction notes

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