Isobutyryl chloride → HCID 86592328, compound

HRID 1269556Notes

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])=[CH:15][CH:14]=2)=[C:7]([Cl:20])[C:6]=1[CH3:21])(=[O:3])[CH3:2].[C:22](Cl)(=[O:26])[CH:23]([CH3:25])[CH3:24]>>[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:22](=[O:26])[CH:23]([CH3:25])[CH3:24])=[CH:15][CH:14]=2)=[C:7]([Cl:20])[C:6]=1[CH3:21])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 62325Isobutyryl chloride

HCID 86592326HCID 86592326, compound

Product 1

HCID 86592328HCID 86592328, compoundYield 95%

Procedure

Methyl[3,5-dichloro-4-(4-aminophenoxy)phenyl] acetate (33 mg, 0.10 mmol), was coupled with isobutyryl chloride (11 mg), using the method described in Example 1(h). After purification on column (silica gel, ethyl acetate/petrolium ether), 35 mg (95%) of methyl-[3,5-dichloro-4-(4-isobutyramidophenoxy)phenyl] acetate was obtained, which was hydrolysed using the method described in Example 1(i). This gave 30 mg (89%) of 3,5-dichloro-4-(4-isobutyramidophenoxy)phenylacetic acid.

Workup

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

Sources & evidence

ORD record: ord-649eb38e94684e7a8d3bebfe445d254c
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199265B2

Reaction notes

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