Triethylamine → HCID 11505538, compound

HRID 1241530Notes

Reaction equation

HRID 1241530 reaction equation
[Si:1]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[NH:13][C@@H:12]1[CH2:16][C:17]([C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:18])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:39]([O:45][CH2:46][O:47][C:48](=[O:52])[C:49](Cl)=[O:50])(=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41]>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[N:13]([C:49](=[O:50])[C:48]([O:47][CH2:46][O:45][C:39](=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43])=[O:52])[C@@H:12]1[CH2:16][C:17]([C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:18])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10966111[(2-chloro-2-oxoacetyl)oxy]methyl pivalateHCID 11640909HCID 11640909, compound

Product 1

HCID 11505538HCID 11505538, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl) silyl]oxy}-ethyl)-4-oxo-2-azetidinyl]acetyl}benzoate (2.24 g) and triethylamine (1.11 g) were dissolved in dry methylene chloride (10 ml), and thereto was added dropwise a solution of [(2-chloro-2-oxoacetyl)oxy]methyl pivalate (10 mmol) in dry methylene chloride (10 ml) under ice-cooling. The reaction was quenched by addition of saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and separated. The organic layer was washed successively with an aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give tert-butyl 3-({(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl) silyl]oxy}ethyl)-1-[{[(2,2-dimethylpropanoyl)oxy]methoxy}(oxo)acetyl]-4-oxo-2-azetidinyl}acetyl)benzoate (3.152 g).

Workup

  1. temperaturecooling
  2. customThe reaction was quenched by addition of saturated aqueous ammonium chloride solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. customseparated
  5. washThe organic layer was washed successively with an aqueous sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4006c3c74ed544e0ba7c8dce9cbca91d
Source dataset
uspto-grants-2006_10
Patent number
US07115595B2

Reaction notes

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