Nitromethane → 25361-54-0

HRID 2186676Notes

Reaction equation

HRID 2186676 reaction equation
[Cl:1][CH2:2][C:3]([NH2:5])=[O:4].[C:6]1([P:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+](C)([O-])=O>O>[Cl-:1].[C:3]([CH2:2][P+:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)(=[O:4])[NH2:5]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 6580ChloroacetamideHCID 11776Triphenylphosphine

Product 1

HCID 21289225361-54-0

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzhydryl 3-[prop-1′E-ene-3′-amide)]-7Z-[(2″-pyridyl)methylidene]-2-cephem-4-carboxylate (11d). Using a procedure similar to that described by S. Trippet, and D. M. Walker, J. Chem. Soc. 3874, 1959, the requisite ylide (carbamoylmethylenetriphenyl-phosphorane) was obtained as follows: A solution of carbamoylmethyltriphenyl-phosphonium chloride (5 g, 14.0 mmol), (itself obtained from chloroacetamide and triphenylphosphine in refluxing nitromethane) in H2O (75 mL) was cooled to 0° C. and a cold (0-5° C.) solution of NaOH (0.56 g in 5 mL H2O) was added in one portion. The resultant mixture was immediately filtered and washed with cold water (75 mL). The collected precipitate was dried under high vacuum to provide carbamoylmethylenetriphenylphosphorane. This ylide was reacted with aldehyde 10 according to the general procedure above to give the title compound; yield: 78%; 1H NMR (CDCl3): δ 5.41 (s, 1H), 5.70 (d, J=15.5 Hz, 1H), 5.95 (s, 1H), 6.84 (s, 1H), 6.87 (s, 1H), 6.96 (s, 1H), 7.23-7.36 (m, 13H), 7.69-7.72 (m, 2H), 8.60 (d, J=4.12 Hz, 1H).

Sources & evidence

ORD record
ord-78cf9766bb3846dd9a5050b5d5e60297
Source dataset
uspto-grants-2002_06
Patent number
US06407091B1

Reaction notes

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