2-Propanethiol → HCID 58372809, compound

HRID 656781Notes

Reaction equation

HRID 656781 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][CH:27]([SH: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:29][CH:27]([CH3:28])[CH3:26])[CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 63642-PropanethiolHCID 58372796[3-(2-Bromomethyl-4-nitro-phenoxy)-4-chloro-phenyl]acetic acid ethyl ester

Product 1

HCID 58372809HCID 58372809, compound

Procedure

[3-(2-Bromomethyl-4-nitro-phenoxy)-4-chloro-phenyl]-acetic acid ethyl ester was treated with 2-propanethiol as described in Example 21, Step 8 to provide [4-chloro-3-(2-isopropylsulfanylmethyl-4-nitro-phenoxy)-phenyl]-acetic acid ethyl ester, which was reduced to [3-(4-amino-2-isopropylsulfanylmethyl-phenoxy)-4-chloro-phenyl]-acetic acid ethyl ester as described in Example 21, Step 9. Treatment of the amine with pivaloyl chloride as described in Example 21, Step 10 provided {4-chloro-3-[4-(2,2-dimethyl-propionylamino)-2-isopropylsulfanylmethyl-phenoxy]-phenyl}-acetic acid ethyl ester. Hydrolysis of the ester to the acid was carried out as described in Example 21, Step 11.

Sources & evidence

ORD record
ord-c208eeb4b92d4c1295543397b4e0eabf
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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