2-Mercaptoethanol → HCID 70569286, compound

HRID 1680641Notes

Reaction equation

HRID 1680641 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][CH2:12][CH2:13][OH:14].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[OH:14][CH2:13][CH2:12][S:11][CH2:10]/[CH:9]=[C:6]1/[CH2:7][N:8]2[C@H:4]([O:5]/1)[CH2:3][C:2]2=[O:1]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 7187Benzoyl PeroxideHCID 22807221HCID 22807221, compound

Product 1

HCID 70569286HCID 70569286, 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 2-mercaptoethanol (0.4 ml) and benzoyl peroxide (10 mg). The resulting mixture was stirred under dry nitrogen while being irradiated using a 200 W bulb placed 1" from the reaction vessel for a total time of 14 hours. The mixture was diluted with ethyl acetate (100 ml) and was washed with saturated sodium bicarbonate solution and saturated brine. The solution was dried (magnesium sulphate) and the solvent was evaporated under reduced pressure to give a yellow oil. The oil was chromatographed on silica gel (20 g) using graded elution from 1:4 to 1:1 ethyl acetate/petroleum ether (b.p. 60°-80°). The title compound was thus obtained as a colourless gum (45 mg), [α]D22 =+66.8° (c 1.0, CHCl3). νmax (CHCl3): 3370, 1795, 1695 cm-1. δ(CDCl3): 2.40 (1H, br.s, OH), 2.65 (2H, t, J 6 Hz), 2.95 (1H, d, J 16 Hz), 3.15-3.80 (6H, complex), 4.25-4.55 (2H, complex), 5.47 (1H, d, J 2 Hz). m/e: 138 (67%), 96 (100).

Workup

  1. customwhile being irradiated
  2. customfor a total time of 14 hours
  3. washwas washed with saturated sodium bicarbonate solution and saturated brine
  4. dry with materialThe solution was dried (magnesium sulphate)
  5. customthe solvent was evaporated under reduced pressure
  6. customto give a yellow oil
  7. customThe oil was chromatographed on silica gel (20 g)
  8. washelution from 1:4 to 1:1 ethyl acetate/petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-fc791e17b13044ae8d77bb8cec2dfe12
Source dataset
uspto-grants-1981_06
Patent number
US04275067

Reaction notes

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