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

HRID 1644573Notes

Reaction equation

HRID 1644573 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-d2849d80d89e496e8a0109000439ec8f
Source dataset
uspto-grants-2012_02
Patent number
US08124609B2

Reaction notes

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