HCID 57162144, compound → HCID 57241958, compound

HRID 232823Notes

Reaction equation

HRID 232823 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:17])=[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[CH:14]2[OH:17])=[CH:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

5

Reactant 2

HCID 57162144HCID 57162144, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57241958HCID 57241958, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

0.77 g of (3S,5S)-5-[(7-amidino-9-keto-2-fluorenyl)oxymethyl]-3-carboxymethyl-1-(3-phenylpropyl)-2-pyrrolidinone are dissolved in 15 ml of glacial acetic acid, 0.4 g of 10% palladium/charcoal are added and the mixture is hydrogenated for 24 hours at ambient temperature under 3 bars of hydrogen pressure. The catalyst is filtered off, the filtrate is evaporated down and purified by chromatography over silica gel (eluant:methylene chloride/methanol/glacial acetic acid =3:1:0.1). The crude product obtained is triturated with ether, filtered off and taken up in 50 ml of a mixture of glacial acetic acid and water (1:2). This solution is concentrated until crystallisation begins (about 5 ml). The crystals precipitated are washed with water, acetone and ether.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated down
  3. custompurified by chromatography over silica gel (eluant:methylene chloride/methanol/glacial acetic acid =3:1:0.1)

Sources & evidence

ORD record
ord-8bde9fa46478451a869f70bfc81aacfe
Source dataset
uspto-grants-1997_01
Patent number
US05591769

Reaction notes

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