HCID 136147906, compound → HCID 136377628, compound

HRID 1790822Notes

Reaction equation

HRID 1790822 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9]([O:11][CH2:12][CH:13]([O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:14][O:15][C:16](=[O:32])[C@H:17]([CH:29]([CH3:31])[CH3:30])[NH:18]C(OCC2C=CC=CC=2)=O)=[O:10])[O:5][C@@H:4]([N:53]2[C:63]3[N:62]=[C:60]([NH2:61])[NH:59][C:57](=[O:58])[C:56]=3[N:55]=[CH:54]2)[CH2:3]1>CO.C(OCC)(=O)C.C(O)(=O)C.[Pd]>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9]([O:11][CH2:12][CH:13]([O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:14][O:15][C:16](=[O:32])[C@H:17]([CH:29]([CH3:31])[CH3:30])[NH2:18])=[O:10])[O:5][C@@H:4]([N:53]2[C:63]3[N:62]=[C:60]([NH2:61])[NH:59][C:57](=[O:58])[C:56]=3[N:55]=[CH:54]2)[CH2:3]1

Participants

6

Reactant 1

HCID 136147906HCID 136147906, compound

Product 1

HCID 136377628HCID 136377628, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2′,3′-dideoxy-3′-fluoro-5′-O-[1-(N-CBz-L-valyloxy)-2-stearoyloxy-3-propyloxy carbonyl] guanosine (190 mg), was dissolved in a mixed solvent of methanol (6 ml), ethyl acetate (2 ml) and acetic acid (1 ml). To the solution was added palladium black (30 mg), and the reaction mixture was kept under hydrogen for 2 h. It was then filtered and the filtrate was evaporated and the titled product was isolated by silica gel column. 110 mg.

Workup

  1. filtrationIt was then filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b0b04d3442064b36aaa283cbab828c72
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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