tert-Butyl mercaptan → [3-(2-tert-Butylsulfanylmethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester

HRID 656771Notes

Reaction equation

HRID 656771 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-:21])=[O:20])=[CH:15][C:14]=2[CH2:22]Br)[CH:6]=1.[CH3:25][C:26]([SH:29])([CH3:28])[CH3:27].[CH3:30][O:31][C:32](=[O:55])[CH2:33][C:34]1[CH:39]=[C:38]([Cl:40])[CH:37]=[C:36]([O:41][C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][C:43]=2[CH2:49][S:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH:35]=1.[C:56](Cl)(=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58]>>[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-:21])=[O:20])=[CH:15][C:14]=2[CH2:22][S:29][C:26]([CH3:28])([CH3:27])[CH3:25])[CH:6]=1.[CH3:30][O:31][C:32](=[O:55])[CH2:33][C:34]1[CH:39]=[C:38]([Cl:40])[CH:37]=[C:36]([O:41][C:42]2[CH:47]=[CH:46][C:45]([NH:48][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])=[CH:44][C:43]=2[CH2:49][S:50][C:51]([CH3:52])([CH3:54])[CH3:53])[CH:35]=1

Participants

6

Reactant 4

HCID 6387tert-Butyl mercaptanHCID 62493Pivaloyl chlorideHCID 58372722[3-(2-Bromomethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl esterHCID 58372724[3-(4-Amino-2-tert-butylsulfanylmethyl-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester

Product 2

HCID 58372762[3-(2-tert-Butylsulfanylmethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl esterHCID 58372845{3-[2-Tert-butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-phenoxy]-5-chloro-phenyl}-acetic acid methyl ester

Procedure

[3-(2-tert-Butylsulfanylmethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester was prepared according to the procedure described in Example 21, Step 8, using [3-(2-bromomethyl-4-nitro-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester and 2-methyl-2-propanethiol, which was reduced to [3-(4-amino-2-tert-butylsulfanylmethyl-phenoxy)-5-chloro-phenyl]-acetic acid methyl ester as described in Example 21, Step 9. The amine was treated with pivaloyl chloride as described in Example 21, Step 10 to provide {3-[2-tert-butylsulfanylmethyl-4-(2,2-dimethyl-propionylamino)-phenoxy]-5-chloro-phenyl}-acetic acid methyl ester. Hydrolysis of the ester to the acid was carried out as outlined in Example 21, Step 11.

Sources & evidence

ORD record
ord-57f0ff2a67a94a8090e83e805e874bd6
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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