HCID 131727694, compound → HCID 131727699, compound

HRID 1157361Notes

Reaction equation

HRID 1157361 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([C:17]2[CH:22]=[C:21]([I:23])[C:20]([O-:24])=[C:19]([I:25])[CH:18]=2)=[C:8]2[CH:14]=[C:13]([I:15])[C:11](=[O:12])[C:10]([I:16])=[CH:9]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+].[CH2:31]([O:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:42](=[O:55])[C@H:43]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([N+:52]([O-])=O)[CH:47]=2)[NH2:44])[CH2:38][CH2:37]1)=[O:35])[CH3:32].[H][H]>C(O)C.[Pd]>[CH:1]1[CH:6]=[C:5]([C:7]([C:8]2[CH:9]=[C:10]([I:16])[C:11]([O-:12])=[C:13]([I:15])[CH:14]=2)=[C:17]2[CH:18]=[C:19]([I:25])[C:20](=[O:24])[C:21]([I:23])=[CH:22]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+:29].[CH2:31]([O:33][C:34]([N:36]1[CH2:37][CH2:38][N:39]([C:42](=[O:55])[C@H:43]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([NH2:52])[CH:47]=2)[NH2:44])[CH2:40][CH2:41]1)=[O:35])[CH3:32]

Participants

5

Reactant 2

HCID 131727694HCID 131727694, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131727699HCID 131727699, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

TIPPS-3-nitro-(L)-phenylalanine-4-ethoxycarbonylpiperazide (157 g; 176 mmol) was dissolved in 800 ml of ethanol, admixed with 19.7 g of 10% palladium on activated carbon catalyst and hydrogenated for 3 days by slowly passing through hydrogen. After filtering off the catalyst, the solvent was evaporated under vacuum and the crude product was chromatographically purified over silica gel.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe solvent was evaporated under vacuum
  3. customthe crude product was chromatographically purified over silica gel

Sources & evidence

ORD record
ord-947ba8d9048f41b0956a970de05dfefc
Source dataset
uspto-grants-2010_10
Patent number
US07807681B2

Reaction notes

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