Trichloroacetonitrile → HCID 178476373, compound

HRID 991147Notes

Reaction equation

[CH3:1][C:2]1([CH3:33])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@@H:16]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:15][C@@H:13]2[OH:14])[CH3:10])[C:4](=[O:32])[CH2:3]1.[Cl:34][C:35]([Cl:39])([Cl:38])[C:36]#[N:37].N12CCCN=C1CCCCC2>C(Cl)Cl>[Cl:34][C:35]([Cl:39])([Cl:38])[C:36](=[NH:37])[O:14][CH:13]1[O:15][C@H:16]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:12]1[NH:11][C:9](=[C:5]1[C:4](=[O:32])[CH2:3][C:2]([CH3:33])([CH3:1])[CH2:7][C:6]1=[O:8])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranose (100 mg, 0.21 mmol) and trichloroacetonitrile in CH2Cl2 was cooled to 0° C. and 1,8-diazabicyclo(5.4.0)undec-7-en (2 mg) added. The reaction mixture was stirred at 0° C. for 1.5 h and at room temperature for 2 h. The solution was evaporated, and the residue chromatographed using CHCl3/EtOAc 1:1 as the mobile phase to give 2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-3,4,6-tri-O-acetyl-α,β-D-glucopyranosyl trichloroacetimidate (13) (71 mg, 55%).

Workup

customThe solution was evaporated
customthe residue chromatographed

Sources & evidence

ORD record: ord-491aa0770a9e48259444bfc5857492ef
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462183B1

Reaction notes

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