4-Acetoxy-2-azetidinone → HCID 19605239, compound

HRID 1603664Notes

Reaction equation

HRID 1603664 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([SH:12])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].C(O[CH:17]1[NH:20][C:19](=[O:21])[CH2:18]1)(=O)C>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([S:12][CH:17]2[NH:20][C:19](=[O:21])[CH2:18]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 1199814-Acetoxy-2-azetidinoneHCID 1365393,4-Dimethoxybenzene-1-thiolHCID 5360545Sodium

Product 1

HCID 19605239HCID 19605239, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
5 °C

Procedure

Sodium (0.9 g, 39 mmol) was dissolved in ethanol (150 ml) and 3,4-dimethoxythiophenol (5.9 g, 35 mmol) added dropwise over 20 minutes keeping the temperature between 20° C.-25° C. whilst bubbling nitrogen through the mixture. After 15 minutes, the reaction was cooled to 5° C. and a solution of 4-acetoxyazetidin-2-one (4.3 g, 33 mmol) in ethanol (50 ml) was added dropwise over 15 minutes whilst maintaining the temperature at 5° C. The mixture was stirred at room temperature for 60 minutes and evaporated to dryness under reduced pressure. Water (400 ml) was added, the mixture extracted with dichloromethane (2×300 ml), the extracts dried (MgSO4) and evaporated under reduced pressure to an oil. The oil was cooled to -20° C. and titurated with ether (400 ml) to give a white solid which was isolated by filtration (4.1 g, 52%) m.p. 145-6° C. 1H NMR δ (CDCl3) 2.85 (1H, m, H3a), 3.31 (1H, m, H3b), 3.88 (3H, s, O--CH3), 3.89 (3H, s, O--CH3), 4.92 (1H, dd, J=4.92, 2.30 Hz, H4), 6.30 (1H, br. singlet, N--H), 6.85 (1H, d, J=8.30 Hz, Ph--H), 7.00 (1H, d, J=2.04 Hz, Ph--H), 7.09 (1H, dd, J=8.25, 2.06 Hz, Ph--H).

Workup

  1. custombetween 20° C.-25° C.
  2. custombubbling nitrogen through the mixture
  3. temperaturewhilst maintaining the temperature at 5° C
  4. customevaporated to dryness under reduced pressure
  5. additionWater (400 ml) was added
  6. extractionthe mixture extracted with dichloromethane (2×300 ml)
  7. dry with materialthe extracts dried (MgSO4)
  8. customevaporated under reduced pressure to an oil
  9. temperatureThe oil was cooled to -20° C.
  10. customto give a white solid which
  11. customwas isolated by filtration (4.1 g, 52%) m.p. 145-6° C

Sources & evidence

ORD record
ord-d0274511039c4930a603f3a6d062c29b
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

Loading…