D-1,4-Dithiothreitol → 2-[2-butyl-4-({4-[4-(trifluoromethyl)phenyl]phenyl}methylthio)phenoxy]acetic Acid

HRID 1063763Notes

Reaction equation

HRID 1063763 reaction equation
SC[C@H]([C@@H](CS)O)O.P([O-])(O)(O)=O.[K+].[CH2:15]([C:19]1[CH:30]=[C:29]([S:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=3)=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:20]=1[O:21][CH2:22][C:23]([O:25]C)=[O:24])[CH2:16][CH2:17][CH3:18]>CO>[CH2:15]([C:19]1[CH:30]=[C:29]([S:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:40]=[CH:41][C:42]([C:45]([F:48])([F:46])[F:47])=[CH:43][CH:44]=3)=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:20]=1[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 446094D-1,4-DithiothreitolHCID 516951Monobasic potassium phosphateHCID 22280052Methyl 2-[2-butyl-4-({4-[4-(trifluoromethyl)phenyl]phenyl}methylthio)phenoxy]acetate2×

Product 1

HCID 222801432-[2-butyl-4-({4-[4-(trifluoromethyl)phenyl]phenyl}methylthio)phenoxy]acetic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared in the manner analogous to Example 1D with the product from example 100E (2.79 g, 10.0 mmol), dithiothreitol (3.08 g, 20.0 mmol), and 0.2 M potassium dihydrogenphosphate (15 ml) in 60 ml of methanol. 400 MHz 1H NMR (CDCl3) δ 7.11 (m, 2H), 6.60 (d, 1H), 4.61 (s, 2H), 3.81 (s, 3H), 3.36 (s, 1H), 2.63 (m, 2H), 1.57 (m, 2H), 1.38 (m, 2H), 0.98 (t, 3H). Step 7. Preparation of methyl 2-[2-butyl-4-({4-[4-(trifluoromethyl)phenyl]phenyl}methylthio)phenoxy]acetate (Compound 100G)

Sources & evidence

ORD record
ord-6c6d7cd59e504623b13e5113f1cf77c2
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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