HCID 136333560, compound → Acetate

HRID 1077543Notes

Reaction equation

HRID 1077543 reaction equation
C(OC([NH:11][C:12]1([C:18]([O:20][CH2:21][CH:22]([O:44][CH2:45][N:46]2[CH:54]=[N:53][C:52]3[C:51](=[O:55])[NH:50][C:49]([NH2:56])=[N:48][C:47]2=3)[CH2:23][O:24][C:25]([C:27]2([NH:33]C(OCC3C=CC=CC=3)=O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:26])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=O)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[NH2:33][C:27]1([C:25]([O:24][CH2:23][CH:22]([O:44][CH2:45][N:46]2[CH:54]=[N:53][C:52]3[C:51](=[O:55])[NH:50][C:49]([NH2:56])=[N:48][C:47]2=3)[CH2:21][O:20][C:18]([C:12]2([NH2:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:19])=[O:26])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1.[C:18]([O-:20])(=[O:19])[CH3:12]

Participants

6

Reactant 2

HCID 136333560HCID 136333560, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 175AcetateHCID 135704741HCID 135704741, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediyl bis (N-benzyloxycarbonyl-1-amino-cyclohexanecarboxylate), 2.0 g (2.58 mmol) in glacial acetic acid (30 mL) was added palladium on carbon (10%, 0.5 g) and the mixture was hydrogenated under 1 atmosphere hydrogen overnight at room temperature. The mixture was filtered through Celite and the filtrate concentrated under reduced pressure to a thick oil. Water was added to the residue and the mixture was lyophilized to give 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediyl bis (1-amino-cyclohexanecarboxylate) as an acetate as a white solid. Mass spectrum: MA+ 506; Mw 505. Elemental Analysis: C29H47O12N7.1HOAc.1H2O. Calc.: C 49.49; H 7.02; N 13.93. Found: C 49.32; H 6.97; N 13.89.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure to a thick oil
  3. additionWater was added to the residue

Sources & evidence

ORD record
ord-a65b271c683b4327b5d33736fc0ba561
Source dataset
uspto-grants-1996_08
Patent number
US05543414

Reaction notes

Loading…