4-Hydroxybenzoic Acid → HCID 86647594, compound

HRID 2088343Notes

Reaction equation

HRID 2088343 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.[OH:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1>ClCCl>[OH: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 1354-Hydroxybenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 260703HCID 260703, compound

Product 1

HCID 86647594HCID 86647594, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17-Oximino-5-androsten-3β-ol (9) (0.5 g, 1.6 mmol) was taken in anhydrous dichloromethane (30.0 ml). Dicyclohexylcarbodiimide (DCC) (0.34 g, 1.6 mmol) was added followed by p-hydroxybenzoic acid (0.23 g, 1.6 mmol). Reaction mixture was stirred at room temperature for 24-48 hr and completion of the reaction was monitored by TLC. The reaction mixture was filtered to remove precipitated dicyclohexylurea (DCU). Excess of solvent was removed under vacuum and the product was crystallized from ethyl acetate:petroleum ether (60:80) to yield 17-oximino-5-androsten-3β-yl 4-hydroxybenzoate (15) (0.31 g, 62.0%) mp 177-182° C.

Workup

  1. customReaction mixture
  2. filtrationThe reaction mixture was filtered
  3. customto remove
  4. customprecipitated dicyclohexylurea (DCU)
  5. customExcess of solvent was removed under vacuum
  6. customthe product was crystallized from ethyl acetate:petroleum ether (60:80)

Sources & evidence

ORD record
ord-1b036a7f9f0745bfb4449e47fff966fd
Source dataset
uspto-grants-2013_05
Patent number
US08435975B2

Reaction notes

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