Morpholine → p-Nitrobenzyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(1-morpholinoethylidene)acetate

HRID 325464Notes

Reaction equation

HRID 325464 reaction equation
[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:27](OS(C)(=O)=O)[CH3:28])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C:11](=[O:34])[CH:10]2[NH:35][C:36](=[O:45])[CH2:37][O:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:7])[CH2:3][CH2:2]1.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>C1C=CC=CC=1>[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:27]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)[CH3:28])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C:11](=[O:34])[CH:10]2[NH:35][C:36](=[O:45])[CH2:37][O:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 53642168HCID 53642168, compound

Product 1

HCID 53677004p-Nitrobenzyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(1-morpholinoethylidene)acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(1-methanesulfonyloxyethylidene)acetate (1.12 g) in benzene (11 ml) is added morpholine (0.26 ml) under ice cooling, and the mixture is kept at 10° C. overnight. The reaction mixture is washed with water, dried, and evaporated under reduced pressure. Purification of the obtained residue (1 g) by chromatography over silica gel (10 g) using a mixture of benzene and ethyl acetate (1:2) gives p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(1-morpholinoethylidene)acetate

Workup

  1. washThe reaction mixture is washed with water
  2. customdried
  3. customevaporated under reduced pressure
  4. customPurification of the obtained residue (1 g) by chromatography over silica gel (10 g)
  5. additiona mixture of benzene and ethyl acetate (1:2)

Sources & evidence

ORD record
ord-f0ee2f4d218b4cecb7fef71c6c25b241
Source dataset
uspto-grants-1984_04
Patent number
US04440683

Reaction notes

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