Ozone → HCID 44394458, compound

HRID 1180731Notes

Reaction equation

HRID 1180731 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:29])[O:16][C:17]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])#N.[CH3:49][C@H:50]([NH2:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>ClCCl>[O:1]=[C:6]([NH:57][C@@H:50]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH3:49])[C:7]([C@@H:9]([NH:14][C:15](=[O:29])[O:16][C:17]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:10][CH2:11][CH2:12][CH3:13])=[O:8]

Participants

5

Reactant 3

HCID 24823OzoneHCID 758181-Phenethylamine, (-)-HCID 58979654HCID 58979654, compound

Product 1

HCID 44394458HCID 44394458, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Ozone was bubbled through a solution of 304.6 mg (493.9 μmol) of 1-benzylcyclopentyl(1S)-1-[cyano(triphenylphosphoranylidene)acetyl]pentylcarbamate in 10 mL of dichloromethane at −78° C. for 15 min. The solution was purged with nitrogen for 5 min, then 63.7 μL (493.9 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 16 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 33.4 mg (15%) of 1-benzylcyclopentyl(1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate. Rf=0.23 (1:4 ethyl acetate:hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.19 (d, J=8 Hz, 1H), 8.31-7.11 (m, 11H), 4.98 (p, J=8 Hz, 1H), 4.82-4.74 (m, 1H), 3.18 (s, 2H), 1.94-1.80 (m, 2H), 1.78-1.54 (m, 6H), 1.42 (d, J=7 Hz, 3H), 1.40-1.16 (m, 6H), 0.81 (t, J=7 Hz, 3H); HRMS C28H36N2O4+Na m/z 487.2573 (M+Na)Cal; 487.2568 (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 16 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-e4b90efee6c3427bb7bff7404e5933e2
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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