1,1',1''-Methanetriyltripiperidine → HCID 54010473, compound

HRID 2164323Notes

Reaction equation

HRID 2164323 reaction equation
N1([CH:7]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)N2CCCCC2)CCCCC1.[CH3:20][O:21][P:22]([NH:26][CH:27]1[C:34](=[O:35])[N:33]2[CH:28]1[S:29][CH2:30][C:31]([CH3:49])=[C:32]2[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=1)=[O:37])([O:24][CH3:25])=[O:23]>C(OCC)(=O)C>[CH3:20][O:21][P:22]([NH:26][CH:27]1[C:34](=[O:35])[N:33]2[CH:28]1[S:29][CH2:30][C:31]([CH:49]=[CH:7][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[C:32]2[C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=1)=[O:37])([O:24][CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 126019201,1',1''-MethanetriyltripiperidineHCID 20406364HCID 20406364, compound

Product 1

HCID 54010473HCID 54010473, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
45 °C

Procedure

Tripiperidinomethane (1.06 g) is added to a solution of 7-dimethoxyphosphorylamino-3-methyl-2-(4-nitrobenzyloxycarbonyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.9 g) in ethyl acetate (40 cc) at 45° C., and the reaction mixture is stirred for 18 hours at 45° C. and diluted with ethyl acetate (20 cc). The organic solution is washed with distilled water (3×20 cc) and then with a saturated solution of sodium chloride (2×15 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. The residue obtained is recrystallised from ethyl acetate (5 cc), and 7-dimethoxyphosphorylamino-2-(4-nitrobenzyloxycarbonyl)-8-oxo-3-(2-piperidinovinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (E isomer) (0.2 g) is obtained in the form of an orange-yellow crystalline powder, m.p.=220°-221° C.

Workup

  1. washThe organic solution is washed with distilled water (3×20 cc)
  2. dry with materialwith a saturated solution of sodium chloride (2×15 cc), dried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C
  4. customThe residue obtained
  5. customis recrystallised from ethyl acetate (5 cc)

Sources & evidence

ORD record
ord-e3462358719145afbe4f29ae38dd7cfb
Source dataset
uspto-grants-1985_03
Patent number
US04503220

Reaction notes

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