Methanol → 17alpha-Acetoxy-11beta-hydroxy-21-isovaleryloxy-6alpha-methyl-1,4-pregnadiene-3,20-dione

HRID 1285373Notes

Reaction equation

HRID 1285373 reaction equation
[OH:1][C@H:2]1[CH2:22][C@@:21]2([CH3:23])[C@@H:13]([CH2:14][CH2:15][C@:16]2([O:24][C:25](=[O:27])[CH3:26])[C:17](=[O:20])[CH2:18][OH:19])[C@H:12]2[C@H:3]1[C@:4]1([CH3:30])[C:9]([C@@H:10]([CH3:28])[CH2:11]2)=[CH:8][C:7](=[O:29])[CH:6]=[CH:5]1.C(N(CC)CC)C.[C:38](Cl)(=[O:43])[CH2:39][CH:40]([CH3:42])[CH3:41].CO>C(Cl)Cl>[C:25]([O:24][C@:16]1([C@:21]2([CH3:23])[C@H:13]([C@H:12]3[C@H:3]([C@@H:2]([OH:1])[CH2:22]2)[C@:4]2([CH3:30])[C:9](=[CH:8][C:7](=[O:29])[CH:6]=[CH:5]2)[C@@H:10]([CH3:28])[CH2:11]3)[CH2:14][CH2:15]1)[C:17](=[O:20])[CH2:18][O:19][C:38](=[O:43])[CH2:39][CH:40]([CH3:42])[CH3:41])(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 1313172717-O-Acetyl-6-methylprednisolone

Product 1

HCID 1357889117alpha-Acetoxy-11beta-hydroxy-21-isovaleryloxy-6alpha-methyl-1,4-pregnadiene-3,20-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 4 ml of methylene chloride was dissolved 208 mg of 11β,21-dihydroxy-17α-acetoxy-6α-methyl-1,4-pregnadiene-3,20-dione obtained according to the method as described in Example 6. To this solution was added 202 mg of triethylamine and the solution was cooled externally with ice. To this solution was added slowly a solution of 120 mg of isovaleryl chloride in 1 ml of methylene chloride, and the mixture was stirred for 1.5 hours. To the reaction liquid was added 1 ml of methanol, and the mixture was further stirred for one hour. The reaction liquid was concentrated under reduced pressure and the resultant residue was directly subjected to preparative thin layer chromatography (silica gel) for purification and then recrystallized from ether-hexane whereby 195 mg (yield: 78.0%) of the title compound was obtained as colorless fine needle crystals. Shown below are physical properties and various analytical data of this compound.

Workup

  1. customobtained
  2. temperaturethe solution was cooled externally with ice
  3. customTo the reaction liquid
  4. stirringthe mixture was further stirred for one hour
  5. customThe reaction liquid
  6. concentrationwas concentrated under reduced pressure
  7. customthe resultant residue was directly subjected to preparative thin layer chromatography (silica gel) for purification

Sources & evidence

ORD record
ord-3f9599b7351b4929bfc86d4542d0a957
Source dataset
uspto-grants-1986_01
Patent number
US04567172

Reaction notes

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