Isobutyryl chloride → HCID 86592339, compound

HRID 1269569Notes

Reaction equation

[C:1]([O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([Br:21])[CH:15]=2)=[C:8]([Cl:22])[C:7]=1[CH2:23][CH3:24])(=[O:4])[CH2:2][CH3:3].[C:25](Cl)(=[O:29])[CH:26]([CH3:28])[CH3:27]>>[C:1]([O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])=[C:16]([Br:21])[CH:15]=2)=[C:8]([Cl:22])[C:7]=1[CH2:23][CH3:24])(=[O:4])[CH2:2][CH3:3]

Participants

Reactant 2

HCID 62325Isobutyryl chloride

HCID 86592340HCID 86592340, compound

Product 1

HCID 86592339HCID 86592339, compoundYield 86.1%

Procedure

Ethyl(3,5-dichloro-4-[4-amino-3-bromophenoxy]phenyl) propionate (50 mg) was coupled with isobutyryl chloride (30 mg), using the method described in Example 1(h). After purification on column (silica gel, ethyl acetate/petrolium ether, 1:9), 50 mg of ethyl(3,5-dichloro-4-[3-bromo-4-isobutyramidophenoxy]phenyl) propionate was obtained, which was hydrolysed using the method described in Example 1(i). This gave 40 mg of 3,5-dichloro-4-(3-bromo-4-isobutyramidophenoxy)phenylpropionic acid.

Workup

customAfter purification on column (silica gel, ethyl acetate/petrolium ether, 1:9)

Sources & evidence

ORD record: ord-3ba78f0073ef46979a1ee1737424b28e
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199265B2

Reaction notes

Loading…