tert-Butyl mercaptan → HCID 58372750, compound

HRID 656788Notes

Reaction equation

HRID 656788 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[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]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[CH2:23]Br)[CH:7]=1)[CH3:2].[CH3:26][C:27]([SH:30])([CH3:29])[CH3:28]>>[CH2:1]([O:3][C:4](=[O:25])[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]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[CH2:23][S:30][C:27]([CH3:29])([CH3:28])[CH3:26])[CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6387tert-Butyl mercaptanHCID 58372796[3-(2-Bromomethyl-4-nitro-phenoxy)-4-chloro-phenyl]acetic acid ethyl ester

Product 1

HCID 58372750HCID 58372750, 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.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-00ab100034704b56a41af46248d1c07f
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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