Oxalyl chloride → HCID 53749054, compound

HRID 2051223Notes

Reaction equation

HRID 2051223 reaction equation
[C:1]([C:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2C(O)=O)[CH:6]=1)([O:3][CH3:4])=[O:2].C(Cl)(=O)C(Cl)=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][CH2:14]2)[CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 67926897HCID 67926897, compound

Product 1

HCID 53749054HCID 53749054, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Carbomethoxy-3-androstene-17β-carboxylic acid, (360 mg, 0.78 mmol) was suspended in 10 ml of dry toluene and treated with 0.4 ml of oxalyl chloride for 2 hours under argon. The reaction mixture was then evaporated (1 mm Hg) and the residue was dissolved in 10 ml dry THF. A solution of 0.6 ml diisopropylamine in 2 ml dry THF was added and the reaction mixture stirred for 1 hour. The mixture was diluted with ice water and extracted with dichlorome thane. The organic layer was then washed twice with cold 5% hydrochloric acid, sodium hydroxide and brine; dried over sodium sulfate and evaporated. Chromatography on silica gel eluting with 20% ethyl acetate in hexane followed by recrystallization from diethyl ether afforded 3-carbomethoxy-3-androstene 178 N,N -diisopropylcarboxamide.

Workup

  1. customThe reaction mixture was then evaporated (1 mm Hg)
  2. dissolutionthe residue was dissolved in 10 ml dry THF
  3. additionA solution of 0.6 ml diisopropylamine in 2 ml dry THF was added
  4. additionThe mixture was diluted with ice water
  5. extractionextracted with dichlorome thane
  6. washThe organic layer was then washed twice with cold 5% hydrochloric acid, sodium hydroxide and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customChromatography on silica gel eluting with 20% ethyl acetate in hexane followed by recrystallization from diethyl ether

Sources & evidence

ORD record
ord-97e1ed1a60b64e04bde80fd6be91e67f
Source dataset
uspto-grants-1991_05
Patent number
US05017568

Reaction notes

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