4-Methylmorpholine → HCID 57071692, compound

HRID 893177Notes

Reaction equation

HRID 893177 reaction equation
[CH2:1]([CH:10]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[N:11]1[CH:14]([CH2:15][C:16](O)=[O:17])[CH:13]([CH:19]([O:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:23])[CH3:20])[C:12]1=[O:35])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:45]N1CCOCC1.ClC(OCC)=O.[C:58]([O:64][CH:65](C(C)(C)C)[C:66]1[CH:71]=[CH:70][C:69]([N+:72]([O-:74])=[O:73])=[CH:68][CH:67]=1)(=[O:63])[CH2:59][C:60]([O-:62])=[O:61].[H-].[Na+].O1[CH2:85][CH2:84][CH2:83]C1>C(Cl)Cl>[CH2:36]([CH:10]([CH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1)[N:11]1[CH:14]([CH2:15][C:16](=[O:17])[CH:59]([C:60]([O:62][C:84]([CH3:83])([CH3:85])[CH3:45])=[O:61])[C:58]([O:64][CH2:65][C:66]2[CH:67]=[CH:68][C:69]([N+:72]([O-:74])=[O:73])=[CH:70][CH:71]=2)=[O:63])[CH:13]([CH:19]([O:21][C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)=[O:23])[CH3:20])[C:12]1=[O:35])[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 57253280HCID 57253280, compoundHCID 131716436HCID 131716436, compound

Product 1

HCID 57071692HCID 57071692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.8 g of 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-carboxymethyl-2-azetidinone was dissolved in 20 ml of dried methylene chloride, and 0.17 ml of N-methylmorpholine was added thereto. After cooling to -10° C. or less, 0.15 ml of ethyl chloroformate was added dropwise thereto, followed by stirring for 30 minutes. Separately, 0.81 g of t-butyl-(p-nitrobenzyl) malonate was dissolved in 15 ml of dried tetrahydrofuran, and 0.14 g of sodium hydride (50% purity) was added to the resulting solution in a nitrogen stream under ice-cooling, followed by stirring at that temperature for 30 minutes. The resulting solution was added dropwise to the above prepared solution of a mixed anhydride at a temperature of -10° C. or less, followed by stirring for 1 hour. The reaction mixture was warmed to room temperature and concentrated under reduced pressure. The concentrate was diluted with cool water and ethyl acetate, washed successively with a 1N aqueous solution of hydrochloric acid and water, dried over sodium sulfate and distilled off to remove the solvent. The resulting residue was purified by silica gel chromatography to obtain 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-[3-t-butoxycarbonyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]-2-azetidinone.

Workup

  1. temperatureAfter cooling to -10° C. or less
  2. temperaturecooling
  3. stirringby stirring at that temperature for 30 minutes
  4. stirringby stirring for 1 hour
  5. concentrationconcentrated under reduced pressure
  6. additionThe concentrate was diluted with cool water and ethyl acetate
  7. washwashed successively with a 1N aqueous solution of hydrochloric acid and water
  8. dry with materialdried over sodium sulfate
  9. distillationdistilled off
  10. customto remove the solvent
  11. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e970078c246c4aeaa5cf6cb27cb2769b
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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