4-Nitrobenzoic Acid → HCID 86647590, compound

HRID 2088339Notes

Reaction equation

HRID 2088339 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.[N+:38]([C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][CH:42]=1)([O-:40])=[O:39]>ClCCl>[N+:38]([C:41]1[CH:42]=[CH:43][C:44]([C:45]([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:46])=[CH:48][CH:49]=1)([O-:40])=[O:39]

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 260703HCID 260703, compound

Product 1

HCID 86647590HCID 86647590, compoundYield 68%

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), p-nitrobenzoic acid (0.27 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-nitrobenzoate (11) (0.34 g, 68.0%) mp 185-188° 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-32dfef6713044e6e884a2bfe1def42a0
Source dataset
uspto-grants-2013_05
Patent number
US08435975B2

Reaction notes

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