1,4-Cyclohexadiene → HCID 10745775, compound

HRID 251515Notes

Reaction equation

HRID 251515 reaction equation
[NH:1]([C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:18]([NH:20][CH2:21][C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])=[O:4].C1CC=CCC=1>CN(C=O)C.[C].[Pd]>[NH:1]([C:32]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 10628222HCID 10628222, compound

Product 1

HCID 10745775HCID 10745775, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

1.3 g of Trt-Gly-Gly-Phe-Gly-OBn (193) obtained in item (3) above was dissolved in 20 ml of DMF to obtain a solution. To the obtained solution were added 0.5 g of a 10% palladium-carbon catalyst and 0.4 g of 1,4-cyclohexadiene, followed by a reaction at room temperature for 30 minutes, to thereby obtain a reaction mixture. The obtained reaction mixture was subjected to filtration to remove the catalyst, thereby obtaining a solution. The solvents were distilled off from the obtained solution under reduced pressure. The resultant residue was purified by silica gel column chromatography (silica gel: Art No. 9365, Silica gel 60, 200-400 mesh, manufactured and sold by Merck KGaA, Germany; eluent: chloroform/methanol ratio=7/1), thereby obtaining 1.0 g of Trt-Gly-Gly-Phe-Gly (190).

Workup

  1. customto obtain a solution
  2. customfollowed by a reaction at room temperature for 30 minutes
  3. customto thereby obtain a reaction mixture
  4. customThe obtained reaction mixture
  5. filtrationwas subjected to filtration
  6. customto remove the catalyst
  7. customobtaining a solution
  8. distillationThe solvents were distilled off from the obtained solution under reduced pressure
  9. customThe resultant residue was purified by silica gel column chromatography (silica gel: Art No. 9365, Silica gel 60, 200-400 mesh, manufactured and sold by Merck KGaA, Germany; eluent: chloroform/methanol ratio=7/1)

Sources & evidence

ORD record
ord-00fb754c032e4aa6ae3f6a15bd76f486
Source dataset
uspto-grants-2011_01
Patent number
US07863408B2

Reaction notes

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