Ozone → HCID 10310975, compound

HRID 1180734Notes

Reaction equation

HRID 1180734 reaction equation
[O:1]=[O+][O-].C([C:6](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:7]([C@@H:9]([NH:14][C:15](=[O:30])[O:16][C:17]1([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])#N.[CH3:50][C@H:51]([NH2:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>ClCCl>[O:1]=[C:6]([NH:58][C@@H:51]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH3:50])[C:7]([C@@H:9]([NH:14][C:15](=[O:30])[O:16][C:17]1([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[CH2:10][CH2:11][CH2:12][CH3:13])=[O:8]

Participants

5

Reactant 3

HCID 24823OzoneHCID 758181-Phenethylamine, (-)-HCID 58979685HCID 58979685, compound

Product 1

HCID 10310975HCID 10310975, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Ozone was bubbled through a solution of 393.0 mg (623.0 μmol) of 1-benzylcyclohexyl (1S)-1-[cyano(triphenylphosphoranylidene)acetyl]pentylcarbamate in 12 mL of dichloromethane at −78° C. for 15 min. The solution was purged with nitrogen for 5 min, then 80.3 μL (623.0 μmol) of (S)-α-methylbenzylamine was added and the solution was stirred at −78° C. for 15 min. The solution was concentrated and 5 mL of a 1 M solution of silver nitrate in tetrahydrofuran:water (4:1) was added and the mixture was stirred for 66 h at room temperature. The solution was extracted with ethyl acetate. The organic layer was washed with 10% citric acid, followed by saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with an ethyl acetate:hexanes solution (1:4) to give 115.6 mg (39%) of 1-benzylcyclohexyl(1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate. Rf=0.30 (1:4 ethyl acetate:hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.18 (d, J=8 Hz, 1H), 7.36-7.06 (m, 11H), 4.98 (p, J=8 Hz, 1H), 4.82-4.74 (m, 1H), 3.10 (s, 2H), 2.01 (d, J=12 Hz, 2H), 1.80-1.10 (m, 14H), 1.42 (d, J=7 Hz, 3H), 0.82 (t, J=7 Hz, 3H); HRMS C29H38N2O4+Na m/z 501.2729 (M+Na)Cal; 501.2711 (M+Na)Obs.

Workup

  1. customThe solution was purged with nitrogen for 5 min
  2. concentrationThe solution was concentrated
  3. addition5 mL of a 1 M solution of silver nitrate in tetrahydrofuran:water (4:1) was added
  4. stirringthe mixture was stirred for 66 h at room temperature
  5. extractionThe solution was extracted with ethyl acetate
  6. washThe organic layer was washed with 10% citric acid
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography
  11. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-36de3db25d4145cfa92c8a40e466cda7
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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