Acetone → 21-Desacetoxy-21-Chloro Anecortave

HRID 66551Notes

Reaction equation

HRID 66551 reaction equation
[Cl:1][CH:2]=[C:3]([O:25]C)[C@:4]1([OH:24])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C1COCC1.CC(C)=O.Cl>CCCCCC.CO>[Cl:1][CH2:2][C:3](=[O:25])[C@:4]1([OH:24])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8673851121-Chloro-17alpha-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one

Product 1

HCID 1303765421-Desacetoxy-21-Chloro Anecortave

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one (VII, Example 4, 1.0 g), THF (4 ml), acetone (4.9 ml), and methanol (1.4 ml) are mixed. Aqueous hydrochloric acid (6 N, 0.44 ml) is added and the resulting slurry heated at 40° for 1.5 hours. The mixture is cooled to 20°-25° and diluted with hexane (3 ml). The solids are isolated by filtration and washed with hexane/ethyl acetate (85/15, 13 ml) to give the title compound.

Workup

  1. temperaturethe resulting slurry heated at 40° for 1.5 hours
  2. temperatureThe mixture is cooled to 20°-25°
  3. customThe solids are isolated by filtration
  4. washwashed with hexane/ethyl acetate (85/15, 13 ml)

Sources & evidence

ORD record
ord-846a8806a8f34412a7df715c710e35fc
Source dataset
uspto-grants-1982_08
Patent number
US04342702

Reaction notes

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