Pyridine → HCID 57029440, compound

HRID 654355Notes

Reaction equation

HRID 654355 reaction equation
[O:1]=[C:2]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[CH:12]([C:14]([OH:16])=O)[CH3:13])=[CH:3]1.N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[C:38]([NH2:42])([CH3:41])([CH3:40])[CH3:39]>C1C=CC=CC=1.C(Cl)Cl.CCCCCC>[CH3:39][C:38]([NH:42][C:14]([C@H:12]([C@@H:11]1[C@:17]2([CH3:25])[C@H:8]([C@H:7]3[C@H:20]([CH2:19][CH2:18]2)[C@:21]2([CH3:24])[C:4](=[CH:3][C:2](=[O:1])[CH2:23][CH2:22]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)[CH3:13])=[O:16])([CH3:41])[CH3:40]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6385Tert-ButylamineHCID 65578Oxalyl chlorideHCID 2205065327-60-6

Product 1

HCID 57029440HCID 57029440, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

A stirred suspension of 3-oxopregn-4-ene-20-carboxylic acid (1.7 g, 5.0 mmole) in benzene (35 mL) was mixed with pyridine (0.56 mL, 6.25 mmole), cooled in an ice-water bath and treated with oxalyl chloride (0.56 mL, 6.45 mmole). The cooling bath was removed and the reaction mixture was stirred for 1.5 hours. The resulting mixture was then cooled in ice and treated slowly with tert-butylamine (2.9 mL, 29 mmole). After thirty minutes, the mixture was diluted with methylene chloride (100 mL), extracted with 5% hydrochloric acid, dried over magnesium sulfate, treated with charcoal, and filtered. The resulting filtrate was concentrated to give a yellow solid which was dissolved in methylene chloride and purified by flash chromatography (hexane-40% ethyl acetate). The product obtained in this way was subjected to flash chromatography again (hexane-30% ethyl acetate) and the resulting product was recrystallized from acetone to give (20S)-N-(1,1-dimethylethyl)-3-oxopregn-4-ene-20-carboxamide. IR 3445, 3375, 1670 cm-1.

Workup

  1. temperaturecooled in an ice-water bath
  2. customThe cooling bath was removed
  3. temperatureThe resulting mixture was then cooled in ice
  4. waitAfter thirty minutes
  5. extractionextracted with 5% hydrochloric acid
  6. dry with materialdried over magnesium sulfate
  7. additiontreated with charcoal
  8. filtrationfiltered
  9. concentrationThe resulting filtrate was concentrated
  10. customto give a yellow solid which
  11. custompurified by flash chromatography (hexane-40% ethyl acetate)
  12. customThe product obtained in this way
  13. customthe resulting product was recrystallized from acetone

Sources & evidence

ORD record
ord-093e2c53e5a34d9fb5ac506b09c4c953
Source dataset
uspto-grants-1992_07
Patent number
US05130424

Reaction notes

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