Testosterone → 17beta-[(Bromoacetyl)oxy]androst-4-en-3-one

HRID 2082007Notes

Reaction equation

HRID 2082007 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.C(=O)(O)[O-].[Na+].[Br:27][CH2:28][C:29](Cl)=[O:30]>C1C=CC=CC=1>[Br:27][CH2:28][C:29]([O:11][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:5]([CH2:4][CH2:3][C@:2]12[CH3:1])[C@:20]1([CH3:21])[C:14](=[CH:15][C:16](=[O:17])[CH2:18][CH2:19]1)[CH2:13][CH2:12]3)=[O:30]

Participants

5

Reactant 3

HCID 6013Testosterone2×HCID 89602Bromoacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 1475073017beta-[(Bromoacetyl)oxy]androst-4-en-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.884 g (0.01 mol) of testosterone in 30 ml of dry benzene was added 1.008 g (0.012 mol) of sodium bicarbonate; then, while stirring, there were introduced dropwise 1.888 g (0.012 mol) of bromoacetyl chloride over a 5 minute period. The reaction mixture was then stirred under reflux for 6 hours until no testosterone could be traced by TLC. (Plates of Silica Gel G and a CHCH3 /CH3OH system were used.) The inorganic residue was filtered while hot, the filtrate was evaporated in vacuo and the residue was recrystallized from methanol, m.p. 144°-145° C., yield 3.2 g (78%). IR (KBr) 1735 (C=O), 1660 (C=O) cm-1. PMR as expected. The product has the formula: ##STR1602##

Workup

  1. stirringThe reaction mixture was then stirred
  2. filtration) The inorganic residue was filtered while hot, the filtrate
  3. customwas evaporated in vacuo
  4. customthe residue was recrystallized from methanol, m.p. 144°-145° C., yield 3.2 g (78%)

Sources & evidence

ORD record
ord-8b1ec7ad264346a68d11c93e2323fd7d
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

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