Glycidyl tosylate, (R)- → HCID 58931216, compound

HRID 388043Notes

Reaction equation

[CH2:1]([NH:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[OH:16])[N:12]=[CH:11][CH:10]=[C:9]2[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH:28]2[CH2:30][CH2:29]2)=[O:26])=[C:20]([Cl:31])[CH:19]=1)=[O:5])[CH3:2].CC1C=CC(S(O[CH2:43][C@H:44]2[CH2:46][O:45]2)(=O)=O)=CC=1>>[CH2:1]([NH:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:43][C@H:44]1[CH2:46][O:45]1)[N:12]=[CH:11][CH:10]=[C:9]2[O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH:28]2[CH2:30][CH2:29]2)=[O:26])=[C:20]([Cl:31])[CH:19]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 154187Glycidyl tosylate, (R)-

HCID 135829404HCID 135829404, compound

Product 1

HCID 58931216HCID 58931216, compoundYield 47.4%

Procedure

The title compound (235.4 mg, 0.474 mmol, 47.4%) was obtained as light yellow crystals from N6-ethyl-4-(3-chloro-4-(((cyclopropylamino)carbonyl)amino)phenoxy)-7-hydroxy-6-quinolinecarboxamide) (440.9 mg, 1.00 mmol) and (2R)oxiran-2-ylmethyl 4-methyl-1-benzenesulfonate, by the same procedure as in Example 7.

Sources & evidence

ORD record: ord-c25ff7f7d6c5457da936d64783ba283a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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