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

HRID 325466Notes

Reaction equation

HRID 325466 reaction equation
[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:32])[N:13]2[C:16](=[C:25](OS(C)(=O)=O)[CH3:26])[C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>C1C=CC=CC=1>[O:1]([CH2:8][C:9]1[S:15][CH:14]2[CH:11]([C:12](=[O:32])[N:13]2[C:16](=[C:25]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH3:26])[C:17]([O:19][CH2:20][C:21]([Cl:23])([Cl:22])[Cl:24])=[O:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 540189622,2,2-Trichloroethyl alpha-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-methanesulfonyloxyethylidene)acetate

Product 1

HCID 540476012,2,2-Trichloroethyl alpha-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-morpholinoethylidene)acetateYield 50%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2,2,2-trichloroethyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-methanesulfonyloxyethylidene)acetate (1.52 g) in benzene (30 ml) is added morpholine (0.48 ml) at beneath 10° C. After stirring for 1 hour, the mixture is washed with water, dried, and evaporated. Purification of the obtained residue by chromatography over silica gel gives 2,2,2-trichloroethyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-morpholinoethylidene)acetate (0.76 g). Yield: 50%.

Workup

  1. washthe mixture is washed with water
  2. customdried
  3. customevaporated
  4. customPurification of the obtained residue by chromatography over silica gel

Sources & evidence

ORD record
ord-7211df7ebd52437185cff28adac7aea2
Source dataset
uspto-grants-1984_04
Patent number
US04440683

Reaction notes

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