1,2-Dichloroethane → HCID 178496192, compound

HRID 1807349Notes

Reaction equation

HRID 1807349 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:26]C)[N:6]2[CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([O-])=[O:22])=[CH:19][CH:18]=1.O1CCOCC1.C(Cl)CCl.[OH:38][N:39]1[C:43](=[O:44])[CH2:42][CH2:41][C:40]1=[O:45]>ClCCl>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:26])[N:6]2[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:38][N:39]2[C:43](=[O:44])[CH2:42][CH2:41][C:40]2=[O:45])=[O:22])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 312751,4-DioxaneHCID 80170N-HydroxysuccinimideHCID 86666431HCID 86666431, compound

Product 1

HCID 178496192HCID 178496192, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[6-amino-8-methoxy-2-(2-methoxyethoxy)purin-9-ylmethyl]benzoate (2 mmol) is dissolved in dichloromethane or dioxane (10 mL) and EDC (2 mmol) is added. To this solution is added N-hydroxysuccinimide (2 mmol) and resulting mixture is stirred at room temperature for 1 hour. The mixture is taken to dryness in vacuo and the crude product is purified by silica gel chromatography to yield 2 mmol of product that is suitable for conjugation reactions involving primary amines.

Workup

  1. customresulting mixture
  2. customthe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-ea21bced2ea14cf18bf02164e3b85f12
Source dataset
uspto-grants-2013_01
Patent number
US08357374B2

Reaction notes

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