8-(3'-Benzyloxybiphenyl-4-ylmethyl-amino)-2',3',5'-tris-o-(tert-butyldimethylsilyl)adenosine → 2',3',5'-Tris-o-(tert-butyl-dimethylsilyl)-8-(3'-hydroxybiphenyl-4-ylmethylamino)-adenosine

HRID 1713297Notes

Reaction equation

HRID 1713297 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23]3[N:24]([C:55]4[N:56]=[CH:57][N:58]=[C:59]([NH2:62])[C:60]=4[N:61]=3)[C@@H:25]3[O:54][C@H:44]([CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[C@@H:35]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C@H:26]3[O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[Si:28]([O:27][C@@H:26]1[C@H:35]([O:36][Si:37]([C:40]([CH3:41])([CH3:42])[CH3:43])([CH3:39])[CH3:38])[C@@H:44]([CH2:45][O:46][Si:47]([C:50]([CH3:51])([CH3:52])[CH3:53])([CH3:48])[CH3:49])[O:54][C@H:25]1[N:24]1[C:55]2[N:56]=[CH:57][N:58]=[C:59]([NH2:62])[C:60]=2[N:61]=[C:23]1[NH:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)=[CH:20][CH:19]=1)([C:31]([CH3:33])([CH3:34])[CH3:32])([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 674544418-(3'-Benzyloxybiphenyl-4-ylmethyl-amino)-2',3',5'-tris-o-(tert-butyldimethylsilyl)adenosine

Product 1

HCID 674557002',3',5'-Tris-o-(tert-butyl-dimethylsilyl)-8-(3'-hydroxybiphenyl-4-ylmethylamino)-adenosineYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(3′-benzyloxybiphenyl-4-ylmethyl-amino)-2′,3′,5′-tris-O-(tert-butyldimethylsilyl)adenosine (0.713 g) and 10% palladium on carbon (55.4 wt % H2O, 0.480 g) in ethyl acetate (11 mL) was stirred at room temperature for 23 hours under a hydrogen atmosphere. The insoluble material was filtered out and the filtrate was concentrated under reduced pressure to give the title compound (0.615 g).

Workup

  1. filtrationThe insoluble material was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e156b14a62b4cb8859616c7f441519c
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

Loading…