Potassium Carbonate → HCID 11330403, compound

HRID 2377043Notes

Reaction equation

HRID 2377043 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:20]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:19][N:18]([C:28]3[CH2:32][CH2:31][C:30](=[O:33])[C:29]=3[CH2:34][C:35]#[N:36])[CH2:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(=O)([O-])[O-:40].[K+].[K+]>CS(C)=O.OO>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:20]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)[CH2:19][N:18]([C:28]3[CH2:32][CH2:31][C:30](=[O:33])[C:29]=3[CH2:34][C:35]([NH2:36])=[O:40])[CH2:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86610916HCID 86610916, compound

Product 1

HCID 11330403HCID 11330403, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 784Hydrogen PeroxideCatalyst

Procedure

To a solution of 5.8 mg (0.0107 mmol) {2-[(3R,4S)-3-({(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethyl}oxy)-4-(4-fluorophenyl)pyrrolidin-1-yl]-5-oxocyclopent-1-en-1-yl}acetonitrile (step C) in 5 drops DMSO was added 10 mg (0.072 mmol) potassium carbonate and 5 drops 30% aq. hydrogen peroxide. The reaction mixture was stirred at RT for 4 h, then the volatiles removed overnight using a nitrogen gas stream. The residue was purified by prep TLC on silica gel eluting with methylene chloride/methanol (9/1). The UV active band (˜Rf=0.7) was isolated to afford the title compound as a glassy clear solid. 1H-NMR (CD3OD): δ: 1.44 (d, 3H, 6.5 Hz), 2.43 (br. s, 2H), 2.76 (br. s, 2H), 3.3-4.45 (m, 8H), 4.77 (q, 1H, 6.5 Hz), 6.98 (t, 2H, 8.5 Hz), 7.18 (m, 2H), 7.72 (s, 2H), 7.83 (s, 1H)ppm. MS: 559.1 (M+H) observed.

Workup

  1. customthe volatiles removed overnight
  2. customThe residue was purified by prep TLC on silica gel eluting with methylene chloride/methanol (9/1)
  3. customThe UV active band (˜Rf=0.7) was isolated

Sources & evidence

ORD record
ord-d1e5fc2099484f53bee9a5760a327f4e
Source dataset
uspto-grants-2008_12
Patent number
US07468437B2

Reaction notes

Loading…