Pyridine → HCID 68140766, compound

HRID 1729668Notes

Reaction equation

HRID 1729668 reaction equation
[Cl:1][C@@:2]1([CH3:30])[C@H:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:29])[C@@H:17]([NH:18]C(=O)COC3C=CC=CC=3)[C@H:5]2[S:4][CH2:3]1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C1C=CC=CC=1.O1CCCC1>[NH2:18][C@@H:17]1[C:16](=[O:29])[N:6]2[C@@H:7]([C:8]([O:10][CH2:11][C:12]([Cl:14])([Cl:13])[Cl:15])=[O:9])[C@@:2]([Cl:1])([CH3:30])[CH2:3][S:4][C@H:5]12

Participants

6

Reactant 3

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 68139434HCID 68139434, compound

Product 1

HCID 68140766HCID 68140766, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2,2-trichloroethyl 3β-chloro-3α-methyl-7β-phenoxyacetamidocepham-4α-carboxylate (2.29 g) in benzene (130 ml) is added pyridine (10 ml) and the mixture is cooled at -60°C in the presence of phosphorous pentachloride (1.51 g) for 2 hours. The reaction mixture is evaporated in vacuo to remove benzene, methanol (250 ml) is added thereto, and the solution kept at room temperature overnight. The solution is concentrated to give a residue which is dissolved in 50% aqueous tetrahydrofuran (50 ml), and the tetrahydrofuran is evaporated after 15 minutes. The residual solution is neutralized with 1N sodium hydroxide, and evaporated to give 2,2,2-trichloroethyl 7β-amino-3β-chloro-3α-methylcepham-4α-carboxylate (1.53 g).

Workup

  1. customThe reaction mixture is evaporated in vacuo
  2. customto remove benzene, methanol (250 ml)
  3. additionis added
  4. concentrationThe solution is concentrated
  5. customto give a residue which
  6. customthe tetrahydrofuran is evaporated after 15 minutes
  7. customevaporated

Sources & evidence

ORD record
ord-3236cfb629ba47eeafdfa5237418c758
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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