tert-Butyl hydroperoxide → HCID 69749030, compound

HRID 1062366Notes

Reaction equation

HRID 1062366 reaction equation
C([O:5]O)(C)(C)C.[Cl:7][C:8]1[CH:13]=[C:12]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1[NH:25][C:26](=[O:34])[C@:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:7][C:8]1[CH:13]=[C:12]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:24])=[O:5])=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH:11]=[CH:10][C:9]=1[NH:25][C:26](=[O:34])[C@:27]([OH:33])([CH3:32])[C:28]([F:30])([F:31])[F:29]

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 56999981HCID 56999981, compound

Product 1

HCID 69749030HCID 69749030, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

t-Butylhydroperoxide (0.36 ml of a 3M solution in toluene) was added to a solution of (R)-N-{2-chloro-4-[4-(methylsulphanyl)phenylsulphonyl]phenyl}-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 2) (0.247 g) and d-10-camphorsulphonic acid (0.012 g) in chloroform (5 ml) and the mixture was stirred at ambient temperature for 64 hours. The reaction mixture was transferred directly to a silica gel Mega Bond Elut column and eluted with 0-80% ethyl acetate/hexane to give the title compound (0.237 g) as a foam. NMR (CDCl3): 1.74 (s, 3H), 2.74 (s, 3H), 4.2 (brs, 1H), 7.79 (d, 2H), 7.89 (dd, 1H), 8.0 (m, 1H), 8.1 (d, 2H) 8.65 (d, 1H), 9.38 (brs, 1H); MS (ESP−): 468; EA: found: C, 43.3; H, 3.1; N, 2.98%; C17H15ClF3NO5S2 requires: C, 43.3; H, 3.1; N, 2.8%.

Workup

  1. washeluted with 0-80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-fe467a3c3274420a9ed0062d67092933
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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