Diethyl Carbonate → HCID 53661323, compound

HRID 483102Notes

Reaction equation

HRID 483102 reaction equation
C(NC(C)C)(C)C.[CH3:8][N:9]1[CH2:12][CH2:11][C:10]1=[O:13].[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17]>O1CCCC1>[CH2:16]([O:15][C:14]([CH:11]1[CH2:12][N:9]([CH3:8])[C:10]1=[O:13])=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 7912DiisopropylamineHCID 1376742H-Azetidin-2-one, 2-methyl-

Product 1

HCID 53661323HCID 53661323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into tetrahydrofuran (20 ml) containing diisopropylamine (1.82 ml) is added 15% n-butyllithium-hexane (7.5 ml), and the mixture is stirred for 25 minutes. To this solution are added 1-methyl-2-azetidinone dropwise at -70° C. and after 20 minutes, diethyl carbonate (1.33 ml). After 2.5 hours stirring, reaction mixture is quenched with 10% hydrochloric acid (15 ml) and extracted with ethyl acetate. The solvent is evaporated to give 1-methyl-2-oxoazetidine-3-carboxylic acid ethyl ester (476 mg). Colorless oil.

Workup

  1. additionis added 15% n-butyllithium-hexane (7.5 ml)
  2. waitafter 20 minutes
  3. stirringAfter 2.5 hours stirring
  4. customreaction mixture
  5. customis quenched with 10% hydrochloric acid (15 ml)
  6. extractionextracted with ethyl acetate
  7. customThe solvent is evaporated

Sources & evidence

ORD record
ord-9ca0b92e4ce04726926e95a5e47c5b67
Source dataset
uspto-grants-1986_03
Patent number
US04578378

Reaction notes

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