HCID 86658267, compound → HCID 46239963, compound

HRID 1043403Notes

Reaction equation

HRID 1043403 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][O:17][P:18]([NH:27][C@@H:28]([CH3:35])[C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])[C@@H:13]([O:36]C(OCC3C=CC=CC=3)=O)[C@:12]2([F:48])[CH3:47])=[C:4]([O:49][CH3:50])[N:3]=1.[H][H]>CO.[Pd]>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][O:17][P:18]([NH:27][C@@H:28]([CH3:35])[C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])([O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:19])[C@@H:13]([OH:36])[C@:12]2([F:48])[CH3:47])=[C:4]([O:49][CH3:50])[N:3]=1

Participants

5

Reactant 2

HCID 86658267HCID 86658267, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 46239963HCID 46239963, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of crude phosphoramidate 7 in MeOH (2.5 mL) was added 5% Pd on charcoal (40 mg). The atmosphere in the flask was exchanged with hydrogen twice. The mixture was stirred at ambient temperature under one atmosphere of hydrogen for 1 h. The mixture was filtered through a short pad of Celite and the filtrate was concentrated. The crude residue was checked by 1H-NMR and 31P-NMR and ratio of two isomers was ca. 17:1 SP isomer (1) and also matched the SP-isomer by thin layer chromatography. 31P-NMR (DMSO-d6): δ 4.91.

Workup

  1. filtrationThe mixture was filtered through a short pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-523ac6e16d664d92b28199821a2697e8
Source dataset
uspto-grants-2013_10
Patent number
US08563530B2

Reaction notes

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