Cyclohexene → HCID 178418962, compound

HRID 8536

Reaction equation

HRID 8536 reaction equation
[C:1]([NH:4][CH:5]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)[C:6]([NH:8][CH:9]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=1)[C:10]([N:12]1[CH2:17][CH:16]([CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[NH:15][C:14](=[O:29])[CH:13]1[CH2:30][C:31]1[N:32]=[CH:33][N:34](CC2C=CC=CC=2)[CH:35]=1)=[O:11])=[O:7])(=[O:3])[CH3:2].C1CCCCC=1>C(O)C.C(O)(=O)C.[Pd]>[C:1]([NH:4][CH:5]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)[C:6]([NH:8][CH:9]([CH2:43][C:44]1[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=1)[C:10]([N:12]1[CH2:17][CH:16]([CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[NH:15][C:14](=[O:29])[CH:13]1[CH2:30][C:31]1[N:32]=[CH:33][NH:34][CH:35]=1)=[O:11])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8079Cyclohexene2×HCID 696527502-acetylamino-N-[2-[2-(1-benzyl-1H-imidazol-4-ylmethyl)-5-naphthalen-2-ylmethyl-3-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)-propionamide

Product 1

HCID 178418962HCID 178418962, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

2-acetylamino-N-[2-[2-(1-benzyl-1H-imidazol-4-ylmethyl)-5-naphthalen-2-ylmethyl-3-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)propionamide, 73, (0.22 g, 0.28 mmol) is dissolved in ethanol/acetic acid (4:1) (3 mL). Cyclohexene (3 mL) and Pd-black are added and the solution is refluxed with periodic replenishment of cyclohexene. The reaction is monitored by TLC and after 2 days is cooled and filtered through Celite to remove the catalyst. The filtrate is concentrated in vacuo to afford an oil which is purified by reverse phase C18 prep HPLC to afford the desired product.

Workup

  1. temperatureis cooled
  2. filtrationfiltered through Celite
  3. customto remove the catalyst
  4. concentrationThe filtrate is concentrated in vacuo
  5. customto afford an oil which
  6. customis purified by reverse phase C18 prep HPLC

Sources & evidence

ORD record
ord-c890d2c1d61a43e1a16a98e903c1d8ab
Source dataset
uspto-grants-2006_08
Patent number
US07087759B2

Linked notes

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