HCID 57162144, compound → HCID 57037379, compound

HRID 232824Notes

Reaction equation

HRID 232824 reaction equation
[C:1]([C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH:9]=[CH:10][C:11]([O:18][CH2:19][C@H:20]4[N:24]([CH2:25][CH2:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:23](=[O:34])[C@H:22]([CH2:35][C:36]([OH:38])=[O:37])[CH2:21]4)=[CH:12][C:13]=3[C:14]2=O)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[H][H]>C(O)(=O)C.[Pd]>[C:1]([C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH:9]=[CH:10][C:11]([O:18][CH2:19][C@H:20]4[N:24]([CH2:25][CH2:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:23](=[O:34])[C@H:22]([CH2:35][C:36]([OH:38])=[O:37])[CH2:21]4)=[CH:12][C:13]=3[CH2:14]2)=[CH:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

5

Reactant 2

HCID 57162144HCID 57162144, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57037379HCID 57037379, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

0.3 g of (3S,5S)-5-[(7-amidino-9-keto-2-fluorenyl)oxymethyl]-3-carboxymethyl-1-(3-phenylpropyl)-2-pyrrolidinone are dissolved in 7 ml of glacial acetic acid, 0.05 g of 10% palladium charcoal are added and the mixture is hydrogenated for 6 hours at 70° C. under 3 bar of hydrogen pressure. The catalyst is filtered off, the filtrate is evaporated down and the product is purified by chromatography on silica gel (eluant:tetrahydrofuran/2N acetic acid=10:1)

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated down
  3. customthe product is purified by chromatography on silica gel (eluant:tetrahydrofuran/2N acetic acid=10:1)

Sources & evidence

ORD record
ord-71c10f2a51284ca385d996e010839595
Source dataset
uspto-grants-1997_01
Patent number
US05591769

Reaction notes

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