Iodoacetic Acid → Iodoacetic acid N-hydroxysuccinimide ester

HRID 1275368Notes

Reaction equation

HRID 1275368 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[I:9][CH2:10][C:11](O)=[O:12].C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[I:9][CH2:10][C:11]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])=[O:12]

Participants

5

Reactant 3

HCID 5240Iodoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 3299230Iodoacetic acid N-hydroxysuccinimide esterYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-Hydroxysuccinimide (1 g, 8.7 mmole), iodoacetic acid (8.7 mmole, 1.6 g), and DCC (8.7 mmole, 1.7 g) were added to 250 mL of EtOAc and the mixture was stirred at room temperature for 5 hours. The mixture was filtered and the filtrate concentrated to dryness in vacuo. The residue was crystallized from ethanol to yield 1.74 g (71%) of white crystals, mp 148-150° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated to dryness in vacuo
  3. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-5627ecce1c4349c0b967f59e94f1ad71
Source dataset
uspto-grants-2000_12
Patent number
US06160128

Reaction notes

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