Pivaloyl chloride → HCID 58372786, compound

HRID 888522Notes

Reaction equation

HRID 888522 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([F:14])[F:13])=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=2[CH2:25][S:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH:6]=1.COC(=O)CC1C=CC(OC(F)F)=C(OC2C=CC(N)=CC=2CSCC(F)(F)F)C=1.[C:63](Cl)(=[O:68])[C:64]([CH3:67])([CH3:66])[CH3:65]>>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([F:14])[F:13])=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:63](=[O:68])[C:64]([CH3:67])([CH3:66])[CH3:65])=[CH:18][C:17]=2[CH2:25][S:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH:6]=1

Participants

4

Reactant 3

HCID 62493Pivaloyl chlorideHCID 58372732HCID 58372732, compoundHCID 58372806HCID 58372806, compound

Product 1

HCID 58372786HCID 58372786, compound

Procedure

{4-Difluoromethoxy-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-difluoromethoxy-phenyl}-acetic acid methyl ester as described in Example 21, Step 9, which was treated with pivaloyl chloride as described in Example 21, Step 10 to provide {4-difluoromethoxy-3-[4-(2,2-dimethyl-propionylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester. Hydrolysis of the ester to the acid was carried out as described in Example 21, Step 11.

Sources & evidence

ORD record
ord-1fbe9396c2d7418fad71c9db4b01e8ad
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

Loading…