Benzoyl Peroxide → HCID 70571125, compound

HRID 1680642Notes

Reaction equation

HRID 1680642 reaction equation
[O:1]=[C:2]1[N:8]2[C@H:4]([O:5][C:6]([CH:9]=[CH2:10])=[CH:7]2)[CH2:3]1.[SH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([S:11][CH2:10]/[CH:9]=[C:6]2/[CH2:7][N:8]3[C@H:4]([O:5]/2)[CH2:3][C:2]3=[O:1])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 2401474-MercaptophenolHCID 22807221HCID 22807221, compound

Product 1

HCID 70571125HCID 70571125, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(5R)-7-Oxo-3-vinyl-4-oxa-1-azabicyclo[3.2.0] hept-2-ene (2.5 mmole) in dry tetrahydrofuran (20 ml) was treated with p-mercaptophenol (650 mg) and benzoyl peroxide (10 mg). The resulting solution was stirred under dry nitrogen while being irradiated using a 200 W bulb placed 1" from the reaction vessel for 1 hour. (The temperature of the solution was 25°-30° during this period). The mixture was diluted with ethyl acetate (100 ml) and was washed with water (3×30 ml) and saturated brine (30 ml). The solution was dried (magnesium sulphate) and the solvent was evaporated under reduced pressure to yield a pale yellow gum. The gum was chromatographed on silica gel using ethyl acetate/petroleum ether (b.p. 60°-80°) to give the title compound as a colourless waxy solid (125 mg), [α]D20 =+138.5° (c 1.0, CHCl3), (Found: M+, 263.0585; C13H 13 NO3S requires 263.0616). νmax (CHCl3): 3200, 1790, 1695, 1600, 1580, 1495 cm-1. δ (CDCl3): 2.62 (1H, d, J 16 Hz), 3.10-3.65 (4H, complex), 4.24 (1H, d, J 14 Hz), 4.39 (1H, t, J 7 Hz), 5.25 (1H, d, J 2 Hz), 6.5-6.8 (3H, m), 7.15-7.35 (2H, m). m/e: 263 (M+, 9%), 138 (100), 126 (25), 125 (23), 96 (42).

Workup

  1. customwhile being irradiated
  2. customfor 1 hour
  3. wait(The temperature of the solution was 25°-30° during this period
  4. washwas washed with water (3×30 ml) and saturated brine (30 ml)
  5. dry with materialThe solution was dried (magnesium sulphate)
  6. customthe solvent was evaporated under reduced pressure
  7. customto yield a pale yellow gum
  8. customThe gum was chromatographed on silica gel

Sources & evidence

ORD record
ord-aed73840d1154de4bd3f8e5e351f661c
Source dataset
uspto-grants-1981_06
Patent number
US04275067

Reaction notes

Loading…