Acetic Acid → HCID 54291793, compound

HRID 851403Notes

Reaction equation

HRID 851403 reaction equation
C([Li])CCC.[OH:6][C:7]([C@H:10]1[C@@H:13]([CH2:14][CH:15]=[CH2:16])[N:12]([C:17](=[C:22]([CH3:24])[CH3:23])[C:18]([O:20][CH3:21])=[O:19])[C:11]1=[O:25])([CH3:9])[CH3:8].Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:28].C(O)(=O)C>O1CCCC1>[CH3:23][C:22]([CH3:24])=[C:17]([N:12]1[C@H:13]([CH2:14][CH:15]=[CH2:16])[C@H:10]([C:7]([CH3:9])([O:6][C:27]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=2)=[O:28])[CH3:8])[C:11]1=[O:25])[C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 782054-Nitrobenzyl chloroformateHCID 54541047HCID 54541047, compoundHCID 178418339Butyllithium

Product 1

HCID 54291793HCID 54291793, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of n-butyl lithium (0.46 ml of 1.38 M solution in hexane) was added to a solution of methyl 2-[(3R, 4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (150 mg) in tetrahydrofuran (3 ml) at -70° C. and the mixture was stirred for 15 minutes at -70° C. A solution of p-nitrobenzyl chloroformate (161 mg) in tetrahydrofuran (3.2 ml) was added to the reaction mixture at -70° C. and the mixture was stirred for 10 minutes at -70° C. The mixture was allowed to warm to 0° C. during 30 minutes and stirred at 0° C. for 1.5 hours. Acetic acid (0.043 ml) was added to the mixture at 0° C. and the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate (30 ml) and the solution was washed with brine, aqueous sodium bicarbonate, and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (10 g) eluting with a mixture of hexane and ethyl acetate (10:1-3:1) to give methyl 3-methyl-2-[(3R,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-allylazetidin-1-yl]but-2-enoate (123 mg) as an oil.

Workup

  1. stirringthe mixture was stirred for 10 minutes at -70° C
  2. temperatureto warm to 0° C. during 30 minutes
  3. stirringstirred at 0° C. for 1.5 hours
  4. customthe mixture was evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  6. washthe solution was washed with brine, aqueous sodium bicarbonate, and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica gel (10 g)
  10. washeluting with a mixture of hexane and ethyl acetate (10:1-3:1)

Sources & evidence

ORD record
ord-4aafb163faea412daf68a8c68dbc2c1f
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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