Triethylamine → HCID 58691133, compound

HRID 2376656Notes

Reaction equation

HRID 2376656 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.C([O:22][C@@H:23]1[C@@H:26]([C@H:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH3:28])[C:25](=O)[NH:24]1)(=O)C.S([O-])(O)(=O)=O.[K+]>ClCCl.[I-].[Zn+2].[I-]>[Si:30]([O:29][C@@H:27]([C@@H:26]1[C@@H:25]([CH2:10][C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:11])[NH:24][C:23]1=[O:22])[CH3:28])([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 114603-MethoxyacetophenoneHCID 516920Potassium bisulfateHCID 10935078Azetidon

Product 1

HCID 58691133HCID 58691133, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To m-methoxyacetophenone (7.5 g, 50 mmol) and triethylamine (10.5 ml, 75 mmol) in dichloromethane (200 ml) was dropped at 0° C. under stirring trifluoromethanesulfonic acid trimethylsilyl ester (10.9 ml, 60 mmol) and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added at room temperature (2R,3R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxo-2-azetidinyl acetate (14.4 g, 50 mmol) and zinc iodide (9.6 g, 30 mmol), and the mixture was stirred for 2 hours. To the reaction mixture was added a 5% aqueous potassium hydrogensulfate solution (250 ml), and an organic layer was separated by a separatory funnel. An aqueous layer was extracted with chloroform (100 ml×twice). The extract was combined with the organic layer, dried over magnesium sulfate, filtered and concentrated. The residue was purified with silica gel chromatography (silica gel 400 g, hexane:ethyl acetate=2:1˜0:1) to give (3S,4R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-[2-(3-methoxyphenyl)-2-oxoethyl]azetidin-2-one (15.91 g, yield 84%) as a pale yellowish solid.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customan organic layer was separated by a separatory funnel
  3. extractionAn aqueous layer was extracted with chloroform (100 ml×twice)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography (silica gel 400 g, hexane:ethyl acetate=2:1˜0:1)

Sources & evidence

ORD record
ord-2f31ba28e161422b867225c97fc746f1
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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