Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 58169894, compound

HRID 384025Notes

Reaction equation

HRID 384025 reaction equation
F[B-](F)(F)F.C[O+:7]([CH3:9])[CH3:8].[F:10][C:11]([F:52])([F:51])[C:12]1[CH:13]=[C:14]([C@H:22]([N:24]([CH3:50])[C:25]([N:27]2[CH2:41][CH2:40][C@:30]3([NH:34]C(=O)[CH:32]([C:36]([O:38][CH3:39])=[O:37])[CH2:31]3)[CH2:29][C@@H:28]2[C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=2[CH3:49])=[O:26])[CH3:23])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1>ClCCl>[F:52][C:11]([F:10])([F:51])[C:12]1[CH:13]=[C:14]([C@H:22]([N:24]([CH3:50])[C:25]([N:27]2[CH2:41][CH2:40][C@:30]3([N:34]=[C:8]([O:7][CH3:9])[CH:32]([C:36]([O:38][CH3:39])=[O:37])[CH2:31]3)[CH2:29][C@@H:28]2[C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=2[CH3:49])=[O:26])[CH3:23])[CH:15]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:17]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 58169871HCID 58169871, compound2×

Product 1

HCID 58169894HCID 58169894, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Trimethyloxonium tetrafluoroborate (10.35 mg, 0.070 mmol) and methyl (5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-2-oxo-1,8-diazaspiro[4.5]decane-3-carboxylate (Intermediate 35, 36 mg) in Dichloromethane (DCM) (2 ml) was stirred at rt for 2 hrs. The mixture was washed with NaHCO3 saturated solution and the aqueous layer was extracted with DCM. The organic layers were combined, filtered through a phase separator tube and concentrated obtaining the intermediate methyl(5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methy)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-2-(methyloxy)-1,8-diazaspiro[4.5]dec-1-ene-3-carboxylate:

Workup

  1. washThe mixture was washed with NaHCO3 saturated solution
  2. extractionthe aqueous layer was extracted with DCM
  3. filtrationfiltered through a phase separator tube
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e3d642477a2421c95d4d40709264089
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

Loading…