4-Aminobenzoic Acid → HCID 86647593, compound

HRID 2088342Notes

Reaction equation

HRID 2088342 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N:11](=[C:13]1[CH2:18][CH2:17][C@H:16]2[C@H:19]3[C@H:29]([CH2:30][CH2:31][C@:14]12[CH3:15])[C@:27]1([CH3:28])[C:22]([CH2:23][C@@H:24](O)[CH2:25][CH2:26]1)=[CH:21][CH2:20]3)[OH:12].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][C@H:24]2[CH2:25][CH2:26][C@@:27]3([CH3:28])[C:22](=[CH:21][CH2:20][C@@H:19]4[C@@H:29]3[CH2:30][CH2:31][C@@:14]3([CH3:15])[C@H:16]4[CH2:17][CH2:18][C:13]3=[N:11][OH:12])[CH2:23]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 260703HCID 260703, compound

Product 1

HCID 86647593HCID 86647593, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Aminobenzoic acid (0.22 g, 1.6 mmol) was added 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). 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, solvent removed under vacuum and the residue was crystallized from ethyl acetate:petroleum ether (60:80) to obtain 17-oximino-5-androsten-3β-yl 4-aminobenzoate (14) (0.28 g, 56.0%) mp 165-168° C.

Workup

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

Sources & evidence

ORD record
ord-5f4fce05a8ec4027958ad7878ead7627
Source dataset
uspto-grants-2013_05
Patent number
US08435975B2

Reaction notes

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