Succinic anhydride → HCID 7060958, compound

HRID 1709161Notes

Reaction equation

HRID 1709161 reaction equation
[CH3:1][C@@:2]12[C@H:12]3[C@H:13]([OH:26])[CH2:14][C@:15]4([CH3:25])[C@@:19]([OH:24])([C:20]([CH2:22][OH:23])=[O:21])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.[C:27]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28]1>N1C=CC=CC=1>[C:30]([CH2:29][CH2:28][C:27](=[O:33])[O:23][CH2:22][C:20](=[O:21])[C@:19]1([OH:24])[C@:15]2([CH3:25])[C@H:16]([C@H:11]3[C@H:12]([C@H:13]([OH:26])[CH2:14]2)[C@:2]2([CH3:1])[C:8](=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2)[CH2:9][CH2:10]3)[CH2:17][CH2:18]1)([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 22986011-Epicortisol

Product 1

HCID 7060958HCID 7060958, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3.60 g of 11-epi-cortisol and 1.00 g of succinic anhydride in 45 ml of pyridine was stirred for 4 days at room temperatures The reaction was concentrated. The residue was partitioned between methylene chloride and water. The organic phase was partitioned with sodium bicarbonate. The aqueous layer was washed with methylene chloride. The aqueous layer was acidified with 10% aqueous U HCl and was extracted with chloroform. The organic phase was concentrated. The residue was chromatographed on RP2 silica gel (20% ethyl acetate/methylene chloride) to yield the product which was crystallized from hot ethyl acetate to yield 2.00 g of the white, solid product, mp 208-209. Anal. Calcd for C25H34O8. Calcd/Found: C, 64.92/64.24; H, 7.41/7.08

Workup

  1. concentrationwas concentrated
  2. customThe residue was partitioned between methylene chloride and water
  3. customThe organic phase was partitioned with sodium bicarbonate
  4. washThe aqueous layer was washed with methylene chloride
  5. extractionwas extracted with chloroform
  6. concentrationThe organic phase was concentrated
  7. customThe residue was chromatographed on RP2 silica gel (20% ethyl acetate/methylene chloride)
  8. customto yield the product which
  9. customwas crystallized from hot ethyl acetate
  10. customto yield 2.00 g of the white, solid product, mp 208-209

Sources & evidence

ORD record
ord-134adcc51bba47c3a087b62a06fa0be1
Source dataset
uspto-grants-1990_08
Patent number
US04948533

Reaction notes

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