2-Propanethiol → {3-Chloro-5-[4-(2,2-dimethyl-propionylamino)-2-isopropylsulfanylmethyl-phenoxy]-phenyl}-acetic acid methyl ester

HRID 656760Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[CH2:22]Br)[CH:6]=1.[CH3:25][CH:26]([SH:28])[CH3:27].[C:29](Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C:5]1[CH:6]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:15][C:14]=2[CH2:22][S:28][CH:26]([CH3:27])[CH3:25])[CH:8]=[C:9]([Cl:11])[CH:10]=1

Participants

Reactant 3

HCID 63642-Propanethiol

HCID 62493Pivaloyl chloride

HCID 58372722[3-(2-Bromomethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester

Product 1

HCID 58372745{3-Chloro-5-[4-(2,2-dimethyl-propionylamino)-2-isopropylsulfanylmethyl-phenoxy]-phenyl}-acetic acid methyl ester

Procedure

Following the procedures described in Example 21, Step 8 (starting from [3-(2-bromomethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester and 2-propanethiol), Example 21, Step 9, and Example 21, Step 10 (using pivaloyl chloride), {3-Chloro-5-[4-(2,2-dimethyl-propionylamino)-2-isopropylsulfanylmethyl-phenoxy]-phenyl}-acetic acid methyl ester was obtained. Hydrolysis of the ester according to the procedure described in Example 21, Step 11 provided the acid.

Sources & evidence

ORD record: ord-1dcad5ffb1de4614a019b2ea49a77825
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071807B2

Reaction notes

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