Dicyclohexylcarbodiimide → HCID 86647595, compound

HRID 2088344Notes

Reaction equation

HRID 2088344 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.[O:38]([CH2:45][C:46](O)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl>[O:38]([CH2:45][C:46]([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:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19188Phenoxyacetic AcidHCID 260703HCID 260703, compound

Product 1

HCID 86647595HCID 86647595, compoundYield 54%

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) (0.342 g, 1.6 mmol) in anhydrous dichloromethane (30.0 ml), phenoxyacetic acid (0.24 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 phenoxyacetate (16) (0.27 g, 54.0%) mp 118-122° 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-0794f9a0f6c845bb90592f4bab42aabb
Source dataset
uspto-grants-2013_05
Patent number
US08435975B2

Reaction notes

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