Benzene → HCID 14230750, compound

HRID 653293Notes

Reaction equation

HRID 653293 reaction equation
C1C=CC=CC=1.[CH3:7][O:8][C:9]([C@H:11]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH3:25])[C:13](=[O:26])[C@H:12]1[N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37])=[O:10].C1CCN2C(=NCCC2)CC1>C(OCC)(=O)C>[CH3:7][O:8][C:9]([C@@H:11]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH3:25])[C:13](=[O:26])[C@H:12]1[N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37])=[O:10]

Participants

5

Reactant 3

HCID 241BenzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54376896HCID 54376896, compound

Product 1

HCID 14230750HCID 14230750, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 200 ml of benzene are added 8.5 g of cis-1-(2,4-dimethoxybenzyl)-3-phthalimido-2-oxoazetidine-4-carboxylic acid methyl ester and 3.1 g of 1,8-diazabicyclo[5,4,0]-7-undecene, and the mixture is heated under reflux for 72 hours. To the reaction mixture, after cooling, is added 100 ml of ethyl acetate, followed by washing with 100 ml and 50 ml of 1N--HCl, and 100 ml of water in this order. To the resulting mixture is added 100 ml of chloroform and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. To the residue is added 50 ml of ethyl acetate. The resulting insolubles are collected by filtration, and washed with 30 ml of ethyl acetate to yield 6.4 g of crude product, which is recrystallized from 220 ml of ethyl acetate to yield trans-1-(2,4-dimethoxybenzyl)-3-phthalimido-2-oxoazetidine-4-carboxylic acid methyl ester, m.p. 186°-188° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 72 hours
  3. temperatureTo the reaction mixture, after cooling
  4. washby washing with 100 ml and 50 ml of 1N
  5. additionTo the resulting mixture is added 100 ml of chloroform
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. additionTo the residue is added 50 ml of ethyl acetate
  9. filtrationThe resulting insolubles are collected by filtration
  10. washwashed with 30 ml of ethyl acetate
  11. customto yield 6.4 g of crude product, which
  12. customis recrystallized from 220 ml of ethyl acetate

Sources & evidence

ORD record
ord-5f78b48c79be483195e94447f3435a9f
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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