Dicyclohexylcarbodiimide → (R)-9-[4-(N-BOC-L-isoleucyloxy)-2-(stearoyloxymethyl)butyl]guanine

HRID 2113942Notes

Reaction equation

HRID 2113942 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]([CH2:17][O:18][C:19](=[O:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[C:38]([NH:45][C@H:46]([C:51](O)=[O:52])[C@H:47]([CH2:49][CH3:50])[CH3:48])([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:38]([NH:45][C@H:46]([C:51]([O:1][CH2:2][CH2:3][C@@H:4]([CH2:17][O:18][C:19](=[O:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)=[O:52])[C@H:47]([CH2:49][CH3:50])[CH3:48])([O:40][C:41]([CH3:43])([CH3:44])[CH3:42])=[O:39]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 135481053(R)-9-[4-hydroxy-2-(stearoyloxymethyl)butyl]guanine

Product 1

HCID 136377418(R)-9-[4-(N-BOC-L-isoleucyloxy)-2-(stearoyloxymethyl)butyl]guanine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

(R)-9-[4-Hydroxy-2-(stearoyloxymethyl)butyl] guanine (135 mg, 0.26 mmole) and N-BOC-L-isoleucine (180 mg, 0.78 mmole) were coevaporated with dry DMF twice and dissolved in-the same solvent (3.5 ml). To the solution was added 1,3-dicyclohexylcarbodiimide (160 mg, 0.78 mmole) and 4-dimethylaminopyridine (4.8 mg, 0.039 mmole). After reaction for 18 hours, the reaction mixture was filtered through Celite and worked up in a conventional manner. The product was isolated by silica gel column chromatography, eluting at 5% MeOH in CH2Cl2. (Yield 160 mg)

Workup

  1. customAfter reaction for 18 hours
  2. filtrationthe reaction mixture was filtered through Celite
  3. customThe product was isolated by silica gel column chromatography
  4. washeluting at 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-abdc6983c51b42bca1bc70e402eb7b30
Source dataset
uspto-grants-2008_10
Patent number
US07432274B2

Reaction notes

Loading…