Ethyl Acetate → (R)-N-[2-Chloro-4-(N,N-dimethylcarbamoylmethylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 1062392Notes

Reaction equation

HRID 1062392 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:25]=[C:24]([S:26][Si](C(C)C)(C(C)C)C(C)C)[CH:23]=[CH:22][C:21]=1[NH:37][C:38](=[O:46])[C@:39]([OH:45])([CH3:44])[C:40]([F:43])([F:42])[F:41].Cl[CH2:48][C:49]([N:51]([CH3:53])[CH3:52])=[O:50].C(OCC)(=O)C>C1COCC1>[Cl:19][C:20]1[CH:25]=[C:24]([S:26][CH2:48][C:49](=[O:50])[N:51]([CH3:53])[CH3:52])[CH:23]=[CH:22][C:21]=1[NH:37][C:38](=[O:46])[C@:39]([OH:45])([CH3:44])[C:40]([F:41])([F:42])[F:43]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 758862-chloro-N,N-dimethylacetamideHCID 2724141Tetrabutylammonium FluorideHCID 69748868(R)-N-(2-Chloro4-(triisopropylsilylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Product 1

HCID 69751525(R)-N-[2-Chloro-4-(N,N-dimethylcarbamoylmethylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (1.1 ml of a 1M solution in THF) was added to (R)-N-(2-chloro-4-(triisopropylsilylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 28) (0.50 g) in anhydrous THF (5 ml) at −70° C. After 15 minutes 2-chlorodimethylacetamide (0.17 ml) was added and the mixture was allowed to warm up then was stirred at ambient temperature for 45 minutes. Ethyl acetate (80 ml) was added and the mixture was washed with brine (100 ml) then dried and volatile material was removed by evaporation. The residue was purified on a silica gel Mega Bond Elut column eluting with 10-50% ethyl acetate/hexane to give the title compound (0.30 g) as a solid. NMR (CDCl3) 1.72 (s, 3H), 2.97 (s, 3H), 3.08 (s, 3H), 3.71 (s, 2H), 4.76 (s, 1H), 7.32-7.36 (m, 1H), 7.53 (d, 1H), 8.32 (d, 1H), 9.05 (s, 1H); MS (ESP−): 383.

Workup

  1. temperatureto warm up
  2. washthe mixture was washed with brine (100 ml)
  3. customthen dried
  4. customvolatile material was removed by evaporation
  5. customThe residue was purified on a silica gel Mega Bond Elut column
  6. washeluting with 10-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-76a4c2c741974f399b0f8cb2bd4a001e
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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