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Hydrochloric Acid → (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

HRID 1461601
Notes
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Reaction equation

HRID 1461601 reaction equation
Cl[CH2:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])=[CH2:4].C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.Cl.C(OCC)(=O)C>CS(C)=O.O.[Cl-].[Na+].O.C(OCC)C>[OH:30][CH2:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])=[CH2:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 15000239HCID 15000239, compound

Product 1

HCID 15000240(3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

Reagents, catalysts & solvents 4

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 962WaterSolvent
HCID 3283Diethyl EtherSolvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (100 g) in dimethylsulfoxide (800 ml) and water (200 ml) were added cuprous oxide (57.6 g) and p-toluenesulfonic acid (107 g), and the resultant mixture was stirred at 50° C. for 1.5 hours and then cooled down with ice-cooling. Brine (3 liters), 2 N hydrochloric acid (1 liter), ethyl acetate (2 liters) and diethyl ether (2 liters) were poured into the reaction mixture, followed by stirring for 0.5 hour. The aqueous layer was extracted with a mixture of ethyl acetate (1 liter) and diethyl ether (1 liter). The combined extracts were washed successively with brine (2 liters), 5% sodium bicarbonate (2 liters) and brine (2 liters) and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone.

Workup

  1. temperaturecooled down with ice-
  2. temperaturecooling
  3. extractionThe aqueous layer was extracted with a mixture of ethyl acetate (1 liter) and diethyl ether (1 liter)
  4. washThe combined extracts were washed successively with brine (2 liters), 5% sodium bicarbonate (2 liters) and brine (2 liters)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-878a8412500e482980f05df1d7680ba7
Source dataset
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05075435

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes