Hydrochloric Acid → N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamine

HRID 1086976Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[C:15]([O:18][CH:19]1[O:33][C@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:20]1[NH2:21])(=[O:17])[CH3:16].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:21][C@@H:20]1[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:33][CH:19]1[O:18][C:15](=[O:17])[CH3:16])=[O:7]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of m-iodobenzoic acid (1.6 g; 6.45×10-3 mol) and thionyl chloride (10 ml) was stirred at 65° C. for 24 hours, benzene was added thereto, and excessive thionyl chloride was removed by distillation under reduced pressure. The thus prepared m-iodobenzoyl chloride was dissolved in benzene (2 ml), and a solution of 1,3,4,6-tetra-O-acetyl-D-glucosamine (2 g; 5.76×10-3 mol) in benzene (10 ml) and pyridine (2 ml) was added thereto, followed by stirring for 48 hours. The resulting mixture was neutralized with 0.1N hydrochloric acid and extracted with chloroform, followed by crystallization from methanol to give N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamine (ABGA) (1.50 g).

Workup

customexcessive thionyl chloride was removed by distillation under reduced pressure
dissolutionThe thus prepared m-iodobenzoyl chloride was dissolved in benzene (2 ml)
stirringby stirring for 48 hours
extractionextracted with chloroform
customfollowed by crystallization from methanol

Sources & evidence

ORD record: ord-e2a6f5ca54c547518b5178e2b31a1f0f
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034212

Reaction notes

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