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Hydrochloric Acid → (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

HRID 329675
Notes
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Reaction equation

HRID 329675 reaction equation
[Si]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:25])[C:16](=[O:24])[CH2:17][C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[NH:13][C:12]1=[O:26])[CH3:10])(C(C)(C)C)(C)C.Cl.OP([O-])([O-])=O.[K+].[K+]>CO.C(OC(=O)C)C.O>[OH:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:25])[C:16](=[O:24])[CH2:17][C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[NH:13][C:12]1=[O:26])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 24450Potassium Phosphate, DibasicHCID 14138755(3S,4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

Product 1

HCID 14329059(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinoneYield 89%

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

The keto ester 2 (1.047 g, 2.73 mmol) in methanol (12.3 ml) was treated with 6N HCl (1.37 ml, 8.22 mmol, 3 eg) and stirred 1 hour at room temperature. The solution was treated with 1M K2HPO4 (8.2 ml) and stirred a few minutes, then diluted with ethylacetate and water. The organic layer was separated, washed with 5% NaHCO3 and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to give the product 3 (0.653 g, 89%) as a clear oil.

Workup

  1. stirringstirred a few minutes
  2. customThe organic layer was separated
  3. washwashed with 5% NaHCO3 and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-0ae4142789d4493380135c93e84eb8fa
Source dataset
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04892869

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes