Hydrochloric Acid → 4-[(3,20-Dioxopregn-4-en-11-yl)oxy]-4-oxobutanoic acid

HRID 2058155Notes

Reaction equation

HRID 2058155 reaction equation
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:24])[CH2:9][C@@H:10]([OH:23])[C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][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>[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:24])[CH2:9][CH:10]([O:23][C:25]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:31])[C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 9273011alpha-Hydroxyprogesterone

Product 1

HCID 1249334-[(3,20-Dioxopregn-4-en-11-yl)oxy]-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

According to the general principles outlined by Erlanger et al. (Method in Immunology and Immunochemistry Vol. I, p. 148, Ed. C. A. Williams and M. W. Chase. Academic Press N.Y., 1967), and by Buzby et al. (J. Med. Chem. 10:199, 1967), a solution of 11α-hydroxyprogesterone (10 g) (Sigma Chem. Co., St. Louis, MO) and of succinic anhydride (10 g) in dry pyridine (100 ml) was prepared and refluxed under nitrogen atmosphere for 20 hours. The cooled reaction mixture was poured into cold aqueous hydrochloric acid (3 N, 500 ml) containing crushed ice, and extracted with chloroform. After evaporation of the chloroform, the residue was recrystallized repeatedly from acetone-hexane, and from acetone yielding 4.5 gm of white crystals, melting point 148°-152° C. Absorption maximum in 0.1 NaOH was at 243 nm. These characteristics were consistent with those described in the literature (Lindner et al., Steroids 19:357-375, 1972) for 11α-hydroxyprogesterone hemisuccinate.

Workup

  1. temperaturerefluxed under nitrogen atmosphere for 20 hours
  2. customThe cooled reaction mixture
  3. additioncontaining
  4. customcrushed ice
  5. extractionextracted with chloroform
  6. customAfter evaporation of the chloroform
  7. customthe residue was recrystallized repeatedly from acetone-hexane
  8. customAbsorption maximum in 0.1 NaOH

Sources & evidence

ORD record
ord-b217ad8f758a40eca1c4a50a7c9394ee
Source dataset
uspto-grants-1980_07
Patent number
US04215102

Reaction notes

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