Pivaloyl chloride → HCID 58372710, compound

HRID 656789Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=2[CH2:21][S:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:7]=1)[CH3:2].[CH3:28][C:29]([CH3:34])([CH3:33])[C:30](Cl)=[O:31]>>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:30](=[O:31])[C:29]([CH3:34])([CH3:33])[CH3:28])=[CH:16][C:15]=2[CH2:21][S:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:7]=1)[CH3:2]

Participants

Reactant 2

HCID 62493Pivaloyl chloride

HCID 58372831HCID 58372831, compound

Product 1

HCID 58372710HCID 58372710, compound

Procedure

As described for Example 21, [3-(2-bromomethyl-4-nitro-phenoxy)-4-chloro-phenyl]-acetic acid ethyl ester and 2-methyl-2-propanethiol were reacted to provide [3-(2-tert-butylsulfanylmethyl-4-nitro-phenoxy)-4-chloro-phenyl]-acetic acid ethyl ester, which was reduced to [3-(4-amino-2-tert-butylsulfanylmethyl-phenoxy)-4-chloro-phenyl]-acetic acid ethyl ester. The amine was treated with trimethylacetyl chloride to provide {3-[2-tert-Butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-phenoxy]-4-chloro-phenyl}-acetic acid ethyl ester. Hydrolysis of the ester provided the acid.

Sources & evidence

ORD record: ord-be22609882bd45d6b9a5b89753a32f57
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071807B2

Reaction notes

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