Benzyl mercaptan → HCID 19605253, compound

HRID 1603639Notes

Reaction equation

HRID 1603639 reaction equation
[Na].[CH2:2]([SH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O[CH:14]1[NH:17][C:16](=[O:18])[CH2:15]1)(=O)C>C(O)C>[CH2:2]([S:9][CH:14]1[NH:17][C:16](=[O:18])[CH2:15]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 1199814-Acetoxy-2-azetidinoneHCID 5360545Sodium

Product 1

HCID 19605253HCID 19605253, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
5 °C

Procedure

Sodium (8.1 g, 0.35 mol) was dissolved in ethanol (250 ml) and benzyl mercaptan (45.2 g, 0.37 mol) 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 (45.0 g, 0.35 mol) in ethanol (50 ml) was added dropwise over 15 minutes whist maintaining the temperature at 5° C. The mixture was stirred at room temperature for 60 minutes and evaporated to dryness under reduced pressure. Water (500 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 (50.2 g, 79%), mp 50-51.0° C.

Workup

  1. custombetween 20° C.-25° C.
  2. custombubbling nitrogen through the mixture
  3. temperaturewhist maintaining the temperature at 5° C
  4. customevaporated to dryness under reduced pressure
  5. additionWater (500 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 (50.2 g, 79%), mp 50-51.0° C.

Sources & evidence

ORD record
ord-eda34a610d2a4c2c8783e9b1f6562851
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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