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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1468310Generated: October 27, 2026

1,1'-Carbonyldiimidazole → N5-(4-hydroxy-3-sulfophenyl)-L-glutamine

https://huagongshe.com/reaction/1468310

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
Reactant(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 6993444—
ReactantHCID 89373065HCID 89373065—
SolventDichloromethaneHCID 6344—
SolventTetrahydrofuranHCID 8028—
ProductN5-(4-hydroxy-3-sulfophenyl)-L-glutamineHCID 123936352—

Reaction Steps

Boc-Glu-OtBu (100 mg, 0.33 mmol) was dissolved in methylene chloride (1 ml) and THF (1 ml), and CDI (65 mg, 1.1 mmol) was added to the solution. The mixture was stirred for 30 minutes at room temperature. Sodium 5-amino-2-hydroxybenzenesulfonate (77 mg, 0.33 mmol) was added to the mixture and stirred overnight at room temperature. After the solvent was removed by distillation, the mixture was purified in accordance with the purification step A. The resulting intermediate was dissolved in 2 ml of TFA. After stirring for 3 hours at room temperature, the solvent was distilled off. The mixture was purified according to the purification step A to give the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09000208B2
Source datasetuspto-grants-2015_04
ORD IDord-da5ed68168a3467994faa085e668d03a
Source noteuspto-grants-2015_04