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

HRID 1285371Notes

Reaction equation

HRID 1285371 reaction equation
[C:1]([O:4][C@:5]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C@@H:24]([OH:28])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:29])[CH:19]=[CH:20]2)[C@@H:15]([CH3:30])[CH2:14]3)[CH2:11][CH2:10]1)[C:6](=[O:9])[CH2:7][OH:8])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CO>C(Cl)Cl>[C:1]([O:4][C@:5]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C@@H:24]([OH:28])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:29])[CH:19]=[CH:20]2)[C@@H:15]([CH3:30])[CH2:14]3)[CH2:11][CH2:10]1)[C:6](=[O:9])[CH2:7][O:8][C:38](=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 1313172717-O-Acetyl-6-methylprednisolone

Product 1

HCID 1357886317alpha-Acetoxy-21-benzoyloxy-11beta-hydroxy-6alpha-methyl-1,4-pregnadiene-3,20-dioneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 4 ml of methylene chloride was dissolved 208 mg of 17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione obtained according to the method described in Example 6. To this solution was added 202 mg of triethylamine, and the mixture was ice-cooled. Next, 140 mg of benzoyl chloride was directly added to the solution and the mixture was stirred for one hour. To the solution was further added 1 ml of methanol, and the mixture was 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 whereby 204 mg (yield: 78.5%) of the title compound was obtained as a colorless amorphous solid. The structure of this compound was confirmed by the following physical properties and results of various analyses:

Workup

  1. customobtained
  2. temperaturecooled
  3. stirringthe mixture was stirred for one hour
  4. customThe reaction liquid
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-817922f4150146e0b44cb789f9fe9bcc
Source dataset
uspto-grants-1986_01
Patent number
US04567172

Reaction notes

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