2-Chloropropionyl chloride → HCID 86592342, compound

HRID 1269571Notes

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].[Cl:25][CH:26]([CH3:30])[C:27](Cl)=[O:28]>>[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:27](=[O:28])[CH:26]([Cl:25])[CH3:30])=[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 1110192-Chloropropionyl chloride

HCID 86592340HCID 86592340, compound

Product 1

HCID 86592342HCID 86592342, compoundYield 93.1%

Procedure

Ethyl(3,5-dichloro-4-[4-amino-3-bromophenoxy]phenyl) propionate (80 mg) was coupled with 2-chloropropionyl chloride (30 mg), using the method described in Example 1(h). After purification on column (silica gel, ethyl acetate/petrolium ether, 1:9), 90 mg of ethyl(3,5-dichloro-4-[3-bromo-4-(2-chloropropionamido)phenoxy]phenyl) propionate was obtained, which was hydrolysed using the method described in Example 1(i). This gave 30 mg of 3,5-dichloro-4-(3-bromo-4-[2-chloropropionamido]phenoxy)phenylpropionic acid.

Workup

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

Sources & evidence

ORD record: ord-2cbe7c51faf24cb99689e69024a0ca38
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199265B2

Reaction notes

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