Triethylamine → HCID 178431948, compound

HRID 614145Notes

Reaction equation

HRID 614145 reaction equation
Br[CH2:2][C:3]([NH:5][CH:6]1[C:19](=[O:20])[N:8]2[CH:9]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[C:10]([CH3:13])([CH3:12])[S:11][C@H:7]12)=[O:4].C(N(CC)CC)C.[SH:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1>C(Cl)Cl>[N:32]1[CH:33]=[CH:34][C:29]([S:28][CH2:2][C:3]([NH:5][CH:6]2[C:19](=[O:20])[N:8]3[CH:9]([C:14]4[NH:18][N:17]=[N:16][N:15]=4)[C:10]([CH3:13])([CH3:12])[S:11][C@H:7]23)=[O:4])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178418431pyridine-4-thiolHCID 178431923HCID 178431923, compound

Product 1

HCID 178431948HCID 178431948, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 1.0 g (0.0028 mole) of 6-(2-bromoacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam in 25 ml of methylene chloride is added 0.28 g (0.0028 mole) of triethylamine. The mixture is stirred at ambient temperature until a clear solution is obtained, and then 0.39 g of 4-mercaptopyridine is added. Stirring is continued for a further 4 hours at ambient temperature, and then the solid which has precipitated is filtered off. It is washed with methylene chloride, followed by ether, to give 0.68 g (78% yield) of 6(2-[4-pyridylthio]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam, m.p. 120° C. (dec.). The infrared spectrum of the product (KBr disc) shows absorption bands at 1790 cm-1 (β-lactam), 1670 cm-1 (amide II). The NMR spectrum (DMSO-d6) shows absorption bands at 9.0-7.0 ppm (multiplet, pyridine hydrogens), 5.9-5.5 ppm (multiplet, C-5 and C-6 hydrogen), 4.0 ppm (singlet, methylene hydrogens), 1.7 ppm (singlet, C-2 methyl hydrogens) and 1.1 (singlet, C-2 methyl hydrogens).

Workup

  1. customis obtained
  2. stirringStirring
  3. customthe solid which has precipitated
  4. filtrationis filtered off
  5. washIt is washed with methylene chloride

Sources & evidence

ORD record
ord-0ff0c1a455be44fd88bb62486fd52444
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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