Triethylamine → HCID 13067887, compound

HRID 2418196Notes

Reaction equation

HRID 2418196 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH:13]1[CH2:16][N:15]([C:17]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([CH3:20])[CH3:19])[C:14]1=[O:25].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:5]([O:4][C:2]([NH:12][CH:13]1[CH2:16][N:15]([C:17]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([CH3:19])[CH3:20])[C:14]1=[O:25])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 13212046HCID 13212046, compound

Product 1

HCID 13067887HCID 13067887, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Benzyl chloroformate (7.9 g.) was dissolved in methylene chloride (50 ml.). A methylene chloride (20 ml.) solution containing 3-amino-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-2-azetidinone (2.42 g.) and triethylamine (3.7 g.) was added dropwise to the solution at -15° to -10° C. in the course of 1.33 hours with stirring, whereafter the mixture was stirred at the same temperature for 1.25 hours. The reaction mixture was evaporated to dryness under reduced pressure to give a residue, which was dissolved in ethyl acetate (150 ml.). The solution was washed three times with 5% hydrochloric acid and once with an aqueous sodium chloride, and then dried over magnesium sulfate. The solvent was removed by distillation and a residue (7.3 g.) was treated with n-hexane to give crude object compound, 3-benzyloxycarbonylamino-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-2-azetidinone (3.27 g.). The compound (3.71 g.) thus obtained was subjected to column chromatography on silica gel (60 g.), and elution was carried out with chloroform and a mixture of chloroform and methanol (volume ratio; 10:1). The fractions containing the desired compound were collected and the solvent was distilled off from the eluate under reduced pressure to give the purified object compound (3.05 g.).

Workup

  1. additionwas added dropwise to the solution at -15° to -10° C. in the course of 1.33 hours
  2. stirringwas stirred at the same temperature for 1.25 hours
  3. customThe reaction mixture was evaporated to dryness under reduced pressure
  4. customto give a residue, which
  5. washThe solution was washed three times with 5% hydrochloric acid
  6. dry with materialonce with an aqueous sodium chloride, and then dried over magnesium sulfate
  7. customThe solvent was removed by distillation
  8. additiona residue (7.3 g.) was treated with n-hexane

Sources & evidence

ORD record
ord-8b413f0cdd3443e39a33afb89f403b20
Source dataset
uspto-grants-1984_09
Patent number
US04472300

Reaction notes

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