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

HRID 67832Notes

Reaction equation

HRID 67832 reaction equation
[CH2:1]([C:8]1[S:14][CH:13]2[CH:10]([C:11](=[O:27])[N:12]2[C:15](=[C:24](O)[CH3:25])[C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(C1SC2C(C(=O)[N:44]2[C:47](=C(OS(C)(=O)=O)C)[C:48]([O:50][CH2:51][C:52](Cl)(Cl)Cl)=O)N=1)C1C=CC=CC=1.N1CCOCC1>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([C:8]1[S:14][CH:13]2[CH:10]([C:11](=[O:27])[N:12]2[C:15](=[C:24]([N:44]2[CH2:47][CH2:48][O:50][CH2:51][CH2:52]2)[CH3:25])[C:16]([O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23])=[O:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 705047432,2,2-Trichloroethyl alpha-[3-benzyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-hydroxyethylidene)-acetateHCID 867365742,2,2-Trichloroethyl alpha-[3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-alpha-(1-methanesulfonyloxyethylidene)acetate

Product 1

HCID 705047462,2,2-Trichloroethyl alpha-[3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]alpha-(1-morpholinoethylidene)acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2,2,2-trichloroethyl α-[3-benzyl-7-oxo-2,6-diaza-4-thiabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate (450 mg) in methylene chloride (7 ml) are added methanesulfonyl chloride (0.093 ml) and triethylamine (0.48 ml) at -25° C., and the mixture is kept at the same temperature for 40 minutes. To the produced solution of 2,2,2-trichloroethyl α-[3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-methanesulfonyloxyethylidene)acetate is added dropwise morpholine (0.112 ml), and the mixture is stirred for 1.3 hours. The reaction mixture is washed with water, dried, and evaporated to give residue which is purified by chromatography over silica gel containing 10% water to give 2,2,2-trichloroethyl α-[3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-morpholinoethylidene)acetate (205 mg).

Workup

  1. washThe reaction mixture is washed with water
  2. customdried
  3. customevaporated
  4. customto give residue which
  5. customis purified by chromatography over silica gel containing 10% water

Sources & evidence

ORD record
ord-b0e5a439898e43e2a876bf38ee18b162
Source dataset
uspto-grants-1982_08
Patent number
US04346218

Reaction notes

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