2,2,2-Trifluoroethanethiol → HCID 58372853, compound

HRID 888511Notes

Reaction equation

HRID 888511 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[CH:26]=O)[CH:7]=1)[CH3:2].C(OC(=O)CC1C=C(C(F)(F)F)C=C(OC2C=CC([N+]([O-])=O)=CC=2CO)C=1)C.[F:57][C:58]([F:62])([F:61])[CH2:59][SH:60]>>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:9]=[C:8]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[CH2:26][S:60][CH2:59][C:58]([F:62])([F:61])[F:57])[CH:7]=1)[CH3:2]

Participants

4

Reactant 3

HCID 41339242,2,2-TrifluoroethanethiolHCID 58372805HCID 58372805, compoundHCID 58372860[3-(2-Formyl-4-nitro-phenoxy)-5-trifluoromethyl-phenyl]acetic acid ethyl ester

Product 1

HCID 58372853HCID 58372853, compound

Procedure

[3-(2-Formyl-4-nitro-phenoxy)-5-trifluoromethyl-phenyl]acetic acid ethyl ester was reduced to [3-(2-hydroxymethyl-4-nitro-phenoxy)-5-trifluoromethyl-phenyl]-acetic acid ethyl ester according to the procedure described in Example 21, Step 6 and then brominated as described in Example 21, Step 7 and then treated with 2,2,2-trifluoroethanethiol to give {3-[4-Nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-5-trifluoromethyl-phenyl}-acetic acid ethyl ester. The amine was reduced as described in Example 21, Step 9, and then treated with pivaloyl chloride as described in Example 21, Step 10 to provide {3-[4-(2,2-Dimethyl-propionylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-5-trifluoromethyl-phenyl}-acetic acid ethyl ester. Hydrolysis of the ester as described in Example 21, Step 11 provided the acid.

Sources & evidence

ORD record
ord-55f178a91cca48bf8c576ed73a7b7fbe
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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