Isobutyryl chloride → HCID 86760482, compound

HRID 1269564Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([Cl:20])[CH:14]=2)=[C:7]([Cl:21])[C:6]=1[CH3:22])(=[O:3])[CH3:2].[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25]>>[C:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])=[C:15]([Cl:20])[CH:14]=2)=[C:7]([Cl:21])[C:6]=1[CH3:22])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 62325Isobutyryl chloride

HCID 86760481HCID 86760481, compound

Product 1

HCID 86760482HCID 86760482, compoundYield 74.2%

Procedure

Methyl[3,5-dichloro-4-(4-amino-3-chlorophenoxy)phenyl] acetate (17 mg) was coupled with isobutyryl chloride (5.0 mg), using the method described in Example 1(h). After purification on column (silica gel, ethyl acetate/petrolium ether, 1:4), 15 mg (74%) of methyl(3,5-dichloro-4-[3-chloro-4-isobutyramidophenoxy]phenyl) acetate was obtained, which was hydrolysed using the method described in Example 1(i). This gave 4 mg (27%) of 3,5-dichloro-4-(4-isobutyramido-3-trifluoromethylphenoxy)phenylacetic acid, m/z 416, 418.

Workup

customAfter purification on column (silica gel, ethyl acetate/petrolium ether, 1:4)

Sources & evidence

ORD record: ord-f572c417e34c49ef9ba69ac042025188
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199265B2

Reaction notes

Loading…