Trifluoroacetic acid → HCID 60031532, compound

HRID 2047454Notes

Reaction equation

HRID 2047454 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])/[CH:15]=[CH:16]/[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([N:32]([CH2:36][Si](C)(C)C)[CH2:33]OC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@H:15]1[C@H:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:36][N:32]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:33]1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@@H:15]1[C@@H:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:36][N:32]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:33]1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium BicarbonateHCID 60031521HCID 60031521, compound

Product 2

HCID 60031522HCID 60031522, compoundYield 28%HCID 60031532HCID 60031532, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of the compound (40.0 g) obtained in step 1 and N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (30.5 g) in toluene (230 mL) was added at 0° C. a solution of trifluoroacetic acid (1.80 mL) in toluene (20 mL), and the mixture was stirred at room temperature for 12 hr. To the reaction mixture was poured saturated aqueous sodium hydrogen carbonate solution, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10→50% ethyl acetate/hexane) to give (4R)-4-benzyl-3-{[(3S,4R)-1-benzyl-4-(4-chlorophenyl)pyrrolidin-3-yl]carbonyl}-1,3-oxazolidin-2-one (20.0 g, 36%) as a less polar compound, and (4R)-4-benzyl-3-{[(3R,4S)-1-benzyl-4-(4-chlorophenyl)pyrrolidin-3-yl]carbonyl}-1,3-oxazolidin-2-one (15.6 g, 28%) as a more polar compound, each as a white powder. property data of less polar compound:

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-08e2351572e243449798bb057edd2342
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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