HCID 136341910, compound → HCID 136341909, compound

HRID 1005361Notes

Reaction equation

HRID 1005361 reaction equation
[C:1]([NH:18][C@H:19]([C:35]([C@@:37]1([N:46]2[C:56]3[N:55]=[C:53]([NH2:54])[NH:52][C:50](=[O:51])[C:49]=3[N:48]=[CH:47]2)[O:45][C@H:42]([CH2:43][OH:44])[C@@H:40]([OH:41])[C@H:38]1[OH:39])=[O:36])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24]C(OCC1C=CC=CC=1)=O)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]>CN(C=O)C.[Pd]>[C:1]([NH:18][C@H:19]([C:35]([C@@:37]1([N:46]2[C:56]3[N:55]=[C:53]([NH2:54])[NH:52][C:50](=[O:51])[C:49]=3[N:48]=[CH:47]2)[O:45][C@H:42]([CH2:43][OH:44])[C@@H:40]([OH:41])[C@H:38]1[OH:39])=[O:36])[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2]

Participants

4

Reactant 1

HCID 136341910HCID 136341910, compound

Product 1

HCID 136341909HCID 136341909, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g of (Nα-FMOC-Nε-CBZ-lysyl)guanosine in 150 mL of DMF was hydrogenated for 3.5 hr at 48 psi in the presence of 0.7 g of 10% Pd/C. The mixture was filtered and the filtrate evaporated and then treated with 30 mL of EtOH followed by 20 mL of H2O. The resulting solid was recrystallized from MeOH-EtOAc.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. additiontreated with 30 mL of EtOH
  4. customThe resulting solid was recrystallized from MeOH-EtOAc

Sources & evidence

ORD record
ord-fcedcc5a493d47e3a9f5254868e63c0b
Source dataset
uspto-grants-2000_04
Patent number
US06054441

Reaction notes

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