4-Chlorobenzoic Acid → HCID 86647589, compound

HRID 2088338Notes

Reaction equation

HRID 2088338 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.[Cl:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1>ClCCl>[Cl:38][C:39]1[CH:47]=[CH:46][C:42]([C:43]([O:22][C@H:14]2[CH2:15][CH2:16][C@@:17]3([CH3:18])[C:12](=[CH:11][CH2:10][C@@H:9]4[C@@H:19]3[CH2:20][CH2:21][C@@:4]3([CH3:5])[C@H:6]4[CH2:7][CH2:8][C:3]3=[N:1][OH:2])[CH2:13]2)=[O:44])=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 260703HCID 260703, compound

Product 1

HCID 86647589HCID 86647589, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of 17-oximino-5-androsten-3β-ol (9) (0.5 g, 1.6 mmol) and dicyclohexylcarbodiimide (DCC) (0.34 g, 1.6 mmol) in anhydrous dichloromethane (30.0 ml), 4-chlorobenzoic acid (0.26 g, 1.6 mmol) was added. The reaction mixture was stirred for 48 hr at room temperature (20-25°) and completion of the reaction was monitored by TLC. The precipitated dicyclohexylurea (DCU) was filtered and the solvent removed under vacuum. The resulting residue was crystallized from ethyl acetate:petroleum ether (60:80) to give 17-oximino-5-androsten-3β-yl 4-chlorobenzoate (10) (0.30 g, 60.0%) mp 167-170° C.

Workup

  1. filtrationThe precipitated dicyclohexylurea (DCU) was filtered
  2. customthe solvent removed under vacuum
  3. customThe resulting residue was crystallized from ethyl acetate:petroleum ether (60:80)

Sources & evidence

ORD record
ord-0b7a143cfc1a423589c097bd5fad551f
Source dataset
uspto-grants-2013_05
Patent number
US08435975B2

Reaction notes

Loading…