HCID 131715911, compound → HCID 21269030, compound

HRID 1194996Notes

Reaction equation

HRID 1194996 reaction equation
[Si]([O:8][C@H:9]([C@@H:11]1[C@@H:14]([S:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[NH:13][C:12]1=[O:23])[CH3:10])(C(C)(C)C)(C)C>O1CCCC1.CO>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([S:15][CH:14]2[NH:13][C:12](=[O:23])[CH:11]2[CH:9]([OH:8])[CH3:10])=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 131715911HCID 131715911, compound

Product 1

HCID 21269030HCID 21269030, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.65 g (4.44 mmol) of ra -(αS*,3S*,4R*)-3-[1-(t-butyldimethylsilyloxy)ethyl]4-[(p-chlorophenyl)thio]-azetidinone are dissolved in 70 ml of tetrahydrofuran/methanol 12 percent hydrochloric acid (4:2:1). The solution is stirred at room temperature for 4 hours and then evaporated. The residue is taken up in 50 ml of ethyl acetate, washed with 20 ml of saturated sodium chloride solution and evaporated. The residue obtained is washed with ether/hexane (1:1) and dried. There is obtained pure rac-(αS*,3S*,4R*)-4-[(p-chlorophenyl)thio]-3-(1-hydroxyethyl)-2-azetidinone; IR: 1760 cm-1.

Workup

  1. customevaporated
  2. washwashed with 20 ml of saturated sodium chloride solution
  3. customevaporated
  4. customThe residue obtained
  5. washis washed with ether/hexane (1:1)
  6. customdried

Sources & evidence

ORD record
ord-0ec729e88e84418b98947c56f758995f
Source dataset
uspto-grants-1989_03
Patent number
US04816581

Reaction notes

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