Thiophenol → HCID 20773303, compound

HRID 1814808Notes

Reaction equation

HRID 1814808 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:5][CH2:4][N:3]1[C:20](=[O:28])[C@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23].C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:20](=[O:28])[C@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:23])[F:24]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 20773304HCID 20773304, compound

Product 1

HCID 20773303HCID 20773303, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (R)-[(2S)-2-methyl-4-(2-nitrobenzenesulphonyl)-1-(3,3,3-trifluoro-2-hydroxy-2-methylpropionyl)piperazine] (Example 26; 19.71 g) in anhydrous DMF (60 ml) was added thiophenol (5.5 ml) followed by anhydrous potassium carbonate (18.7 g). The reaction mixture was allowed to stir at ambient temperature under argon for 4 hours, filtered and washed with DCM (2×300 ml). The filtrate was acidified with HCl (2 M, 250 ml) and the organic phase was separated and discarded. The aqueous phase was adjusted to pH 8 with 2 M NaOH and extracted into EtOAc (5×300 ml). The organic layers were combined, dried and concentrated to give a pale yellow gum which slowly crystallized (4.88 g). NMR (DMSO-d6, 100° C.): 1.21 (d, 3H), 1.54 (s, 3H), 2.49-2.55 (m, 1H), 2.65-2.75 (m, 3H), 2.82-2.91 (m, 2H), 2.97-3.01 (m, 1H), 4.31 (d, 1H), 4.60 (s, 1H); m/z (+ve ESP): 241 (M+H)+.

Workup

  1. filtrationfiltered
  2. washwashed with DCM (2×300 ml)
  3. customthe organic phase was separated
  4. extractionextracted into EtOAc (5×300 ml)
  5. customdried
  6. concentrationconcentrated
  7. customto give a pale yellow gum which
  8. customslowly crystallized (4.88 g)

Sources & evidence

ORD record
ord-0c53cffd164a46a8b1304cbba13e246a
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

Loading…