1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 42614054, compound

HRID 1724640Notes

Reaction equation

HRID 1724640 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([CH2:34][NH2:35])=[N:23][C:24]=2[NH:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)(=O)C.[S:36]([C:40]1[CH:48]=[CH:47][C:43]([C:44](O)=[O:45])=[CH:42][CH:41]=1)([OH:39])(=[O:38])=[O:37].CN(C)CCCN=C=NCC>CN(C)C=O.O>[OH:4][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:14][OH:15])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([CH2:34][NH:35][C:44]([C:43]1[CH:42]=[CH:41][C:40]([S:36]([OH:39])(=[O:38])=[O:37])=[CH:48][CH:47]=1)=[O:45])=[N:23][C:24]=2[NH:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 694694-Sulfobenzoic acidHCID 66911770HCID 66911770, compound

Product 1

HCID 42614054HCID 42614054, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-[2-(aminomethyl)-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate (55 mg, 0.15 mmol) in a mixture of N,N-dimethylformamide (5 ml) and water (10 ml) was added 4-sulfobenzoic acid (37 mg, 0.153 mmol) and 1(3-dimethylaminopropyl)-3-ethylcarbodiimide (28 mg, 0.147 mmol), and the mixture was stirred for 4 hours. Solvent was removed under reduced pressure, and the residue was purified by HPLC, to provide 4-[N-({9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}methyl)carbamoyl]benzenesulfonic acid (39 mg). MS MH+548.57.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-d184a10c13fe4cb8a7f1d6ae6541874f
Source dataset
uspto-grants-2009_02
Patent number
US07488720B2

Reaction notes

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