Morpholine → p-Nitrobenzyl alpha-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-alpha-(1-morpholinoethylidene)acetate

HRID 1155428Notes

Reaction equation

HRID 1155428 reaction equation
C1(P(=O)(O[C:16]([CH3:47])=[C:17]([N:31]2[C:37](=[O:38])[CH:36]3[CH:32]2[S:33][C:34]([CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N:35]3)[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])OC2C=CC=CC=2)C=CC=CC=1.[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>O1CCCC1>[O:40]([CH2:39][C:34]1[S:33][CH:32]2[CH:36]([C:37](=[O:38])[N:31]2[C:17](=[C:16]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[CH3:47])[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)=[O:19])[N:35]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 54307816Phenyl 1-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en-2-yl phenylphosphonate

Product 1

HCID 54060416p-Nitrobenzyl alpha-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-alpha-(1-morpholinoethylidene)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenyl 1-(3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo(3,2,0)hept-2-en-6-yl)-1-(p-nitrobenzyloxycarbonyl)-prop-1-en2-yl phenylphosphonate (1.37 g.) in tetrahydrofuran (20 ml.) at 0°-5° C. was added morpholine (0.383 ml.). After stirring for 3 hours at 0°-5° C., the solvent was evaporated and the residue dissolved in dichloromethane. The resulting solution was washed with water and then with saturated sodium chloride solution, dried with magnesium sulphate and evaporated to give the title compound as a pale yellow foam in essentially quantitative yield. The product obtained was a mixture of geometric isomers (ca. 1:1.4) about the enamine double bond and was identical to that produced in example 8.

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washThe resulting solution was washed with water
  4. dry with materialwith saturated sodium chloride solution, dried with magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-43272ae7641b4d2699d56c9dda5e5f93
Source dataset
uspto-grants-1981_11
Patent number
US04301280

Reaction notes

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