Isobutyryl chloride → HCID 86592343, compound

HRID 1269572Notes

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])=[CH:16][CH:15]=2)=[C:8]([Cl:21])[C:7]=1[CH2:22][CH3:23])(=[O:4])[CH2:2][CH3:3].[C:24](Cl)(=[O:28])[CH:25]([CH3:27])[CH3:26]>>[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:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:16][CH:15]=2)=[C:8]([Cl:21])[C:7]=1[CH2:22][CH3:23])(=[O:4])[CH2:2][CH3:3]

Participants

Reactant 2

HCID 62325Isobutyryl chloride

HCID 86592344HCID 86592344, compound

Product 1

HCID 86592343HCID 86592343, compoundYield 83.5%

Procedure

Ethyl(3,5-dichloro-4-[4-aminophenoxy]phenyl) propionate (80 mg) was coupled with isobutyryl chloride (30 mg), using the method described in Example 1(h). After recrystallization (ethyl acetate/petrolium ether), 80 mg of ethyl(3,5-dichloro-4-[4-isobutyr-amidophenoxy]phenyl) propionate was obtained, which was hydrolysed using the method described in Example 1(i). This gave 50 mg of 3,5-dichloro-4-(4-isobutyramidophenoxy)-phenylpropionic acid, m/z 382.

Workup

customAfter recrystallization (ethyl acetate/petrolium ether)

Sources & evidence

ORD record: ord-67fc59092ded40bba693eb5a9b034165
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199265B2

Reaction notes

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