Benzoic Acid → HCID 86647592, compound

HRID 2088341Notes

Reaction equation

HRID 2088341 reaction equation
[N:1](=[C:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12]([CH2:13][C@@H:14]([OH:22])[CH2:15][CH2:16]1)=[CH:11][CH2:10]3)[OH:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:38](O)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl>[C:38]([O:22][C@H:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:12](=[CH:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:5])[C@H:6]3[CH2:7][CH2:8][C:3]2=[N:1][OH:2])[CH2:13]1)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 260703HCID 260703, compound

Product 1

HCID 86647592HCID 86647592, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17-Oximino-5-androsten-3β-ol (9) (0.5 g, 1.6 mmol) and dicyclohexylcarbodiimide (DCC) (0.34 g, 1.6 mmol) was dissolved in anhydrous dichloromethane (30.0 ml) and stirred. To this was added benzoic acid (0.2 g, 1.6 mmol). The reaction mixture was stirred for 48 hr at room temperature (20-25°) and completion of the reaction was monitored by TLC. The precipitated material was filtered, solvent removed under reduced pressure to give residue which was crystallized from ethyl acetate:petroleum ether (60:80) to get 17-oximino-5-androsten-3β-yl benzoate (13) (0.32 g, 64.0%) mp 165-170° C.

Workup

  1. stirringThe reaction mixture was stirred for 48 hr at room temperature (20-25°) and completion of the reaction
  2. filtrationThe precipitated material was filtered
  3. customsolvent removed under reduced pressure
  4. customto give residue which
  5. customwas crystallized from ethyl acetate:petroleum ether (60:80)

Sources & evidence

ORD record
ord-e54eac870f684c3d8897b038ad91f1ba
Source dataset
uspto-grants-2013_05
Patent number
US08435975B2

Reaction notes

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