Pivaloyl chloride → HCID 58372819, compound

HRID 656777Notes

Reaction equation

HRID 656777 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[CH2:22][S:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:6]=1.COC(=O)CC1C=CC(C)=C(OC2C=CC(N)=CC=2CSCC(F)(F)F)C=1.[C:57](Cl)(=[O:62])[C:58]([CH3:61])([CH3:60])[CH3:59]>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:57](=[O:62])[C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:15][C:14]=2[CH2:22][S:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:6]=1

Participants

4

Reactant 3

HCID 62493Pivaloyl chlorideHCID 58372775HCID 58372775, compoundHCID 58372869HCID 58372869, compound

Product 1

HCID 58372819HCID 58372819, compound

Procedure

Following the procedures described for Example 21, {4-methyl-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester was reduced to {3-[4-amino-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-4-methyl-phenyl}-acetic acid methyl ester and then treated with pivaloyl chloride to provide {3-[4-(2,2-dimethyl-propionylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-4-methyl-phenyl}-acetic acid methyl ester. Hydrolysis of the ester provided the acid.

Sources & evidence

ORD record
ord-e1dbcff969c240edb1f975c53275718d
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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