1,2-Dichloroethane → HCID 178496192, compound

HRID 2200077Notes

Reaction equation

HRID 2200077 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]([OH:26])[N:6]2[CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1.O1CCOCC1.C(Cl)CCl.O[N:38]1[C:42](=[O:43])[CH2:41][CH2:40][C:39]1=[O:44]>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:25]=[CH:24][C:20]([C:21]([O:23][N:38]2[C:42](=[O:43])[CH2:41][CH2:40][C:39]2=[O:44])=[O:22])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 312751,4-DioxaneHCID 80170N-HydroxysuccinimideHCID 178496191HCID 178496191, compound

Product 1

HCID 178496192HCID 178496192, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of example 10 (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 h. 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-dbb5996a7a6a4564b64c8c2d09f4ed70
Source dataset
uspto-grants-2016_06
Patent number
US09359360B2

Reaction notes

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