Hydrochloric Acid → mono N-hydroxysuccinimide glutarate

HRID 1089659

Reaction equation

HRID 1089659 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]1=[O:16].C(N(CC)CC)C.Cl>ClCCl>[C:1]([OH:7])(=[O:8])[CH2:2][CH2:3][CH2:4][C:5]([OH:9])=[O:6].[OH:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]1=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7940Glutaric anhydrideHCID 8471TriethylamineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 19793121mono N-hydroxysuccinimide glutarate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

One mole of glutaric anhydride and one mole of N-hydroxysuccinimide were treated in dichloromethane with 1.2 equivalents of triethylamine. This reaction was stirred for 40 minutes, acidified by the addition of 0.5 N hydrochloric acid (HCl) (aqueous), and then extracted with ethyl acetate to form mono N-hydroxysuccinimide glutarate. This glutarate was then combined with 5 moles of thionyl chloride and stirred at room temperature for three hours. The resulting reaction mixture was dried to remove volatiles, and thereby form N-hydroxysuccinimidyl glutaryl chloride.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-b95aa28f11c3439ea0fb72f54affe916
Source dataset
uspto-grants-1992_01
Patent number
US05079152

Linked notes

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