Methanol → HCID 16657482, compound

HRID 746202Notes

Reaction equation

HRID 746202 reaction equation
CO.C(=O)([O-])[O-].[K+].[K+].C([O:12][CH2:13][C:14](=[O:35])[C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C:24](=[O:34])[CH2:25][CH2:26]2)[CH:21]=[CH:20]3)[CH2:17][CH2:16]1)(=O)C.[CH3:36][C:37]([SH:39])=[O:38]>C(Cl)Cl>[C:37]([S:39][C@@H:20]1[CH2:21][C:22]2[C@:27]([CH3:28])([CH2:26][CH2:25][C:24](=[O:34])[CH:23]=2)[C@@H:29]2[C@@H:19]1[C@H:18]1[C@:32]([CH3:33])([CH2:31][CH2:30]2)[C@@H:15]([C:14](=[O:35])[CH2:13][OH:12])[CH2:16][CH2:17]1)(=[O:38])[CH3:36]

Participants

6

Reactant 4

HCID 887MethanolHCID 10484Thioacetic acidHCID 11430Potassium CarbonateHCID 30807243,20-Dioxopregna-4,6-dien-21-yl acetate

Product 1

HCID 16657482HCID 16657482, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 3 was hydrolyzed by treating 0.5 g of the 21-acetoxy derivative in 8 ml methylene chloride with 10 ml methanol and 4 ml 0.2M aqueous potassium carbonate at room temperature under nitrogen for 30 minutes. The hydrolyzed product was extracted with methylene chloride, washed with water, dried and evaporated. A sample obtained by preparative high performance liquid chromatography showed M+ =404 daltons. An identical product was obtained by a different synthetic route involving alkaline hydrolysis of 21-acetoxy-4,6-pregnadiene-3,20-dione to the C-21-alcohol, followed by reaction with ethanethiolic acid.

Workup

  1. extractionThe hydrolyzed product was extracted with methylene chloride
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customA sample obtained by preparative high performance liquid chromatography
  6. customAn identical product was obtained by a different synthetic route

Sources & evidence

ORD record
ord-680aeeb5c20f494cbe5d0e2bf869ed3a
Source dataset
uspto-grants-1986_07
Patent number
US04603128

Reaction notes

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