Ethyl Acetate → HCID 22287445, compound

HRID 1062393Notes

Reaction equation

HRID 1062393 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:25]=[C:24]([S:26][C:27]2[CH:32]=[CH:31][C:30]([S:33][CH3:34])=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]=1[NH:35][C:36](=[O:54])[C:37]([O:46][Si](C(C)(C)C)(C)C)([C:42]([F:45])([F:44])[F:43])[C:38]([F:41])([F:40])[F:39].C(OCC)(=O)C>C1COCC1>[F:19][C:20]1[CH:25]=[C:24]([S:26][C:27]2[CH:32]=[CH:31][C:30]([S:33][CH3:34])=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]=1[NH:35][C:36](=[O:54])[C:37]([OH:46])([C:38]([F:39])([F:40])[F:41])[C:42]([F:44])([F:45])[F:43]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 22287311HCID 22287311, compound

Product 1

HCID 22287445HCID 22287445, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetra-n-butylammonium fluoride (0.48 ml of a 1M solution in THF) was added to a stirred solution of N-[2-fluoro-4-(4-methylsulphanylphenylsulphanyl)phenyl]-2-(t-butyldimethylsilyloxy)-2-trifluoromethyl-3,3,3-trifluoropropanamide (0.278 g) (Method 55) in anhydrous THF (5 ml) at −78° C. under argon. After 30 minutes ethyl acetate (50 ml) was added and the mixture was washed with aqueous hydrochloric acid (2M, 30 ml) and brine (30 ml) then dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column eluting with 10-30% ethyl acetate/iso-hexane to give the title compound (0.199 g) as a pale yellow solid. NMR (CDCl3): 2.50 (s, 3H), 5.12 (s, 1H), 6.98 (d, 1H), 7.05 (d, 1H), 7.23 (d, 2H), 7.35 (d, 2H), 8.05-8.08 (m, 1H); MS (ESP−): 458,

Workup

  1. washthe mixture was washed with aqueous hydrochloric acid (2M, 30 ml) and brine (30 ml)
  2. customthen dried
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified on a silica gel Mega Bond Elut column
  5. washeluting with 10-30% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-e0769bbed77a48b2adae86b686378119
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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