Pyridine → HCID 70604553, compound

HRID 1764393Notes

Reaction equation

HRID 1764393 reaction equation
[NH2:1][CH:2]1[C:30](=[O:31])[N:4]2[CH:5]([C:10]3[N:14]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:18][CH:17]=4)[N:13]=[N:12][N:11]=3)[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.N1C=CC=CC=1.[C:38]1([CH2:44][C:45](Cl)=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)(Cl)Cl>[C:38]1([CH2:44][C:45]([NH:1][CH:2]2[C:30](=[O:31])[N:4]3[CH:5]([C:10]4[N:14]([CH2:15][C:16]5[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)=[CH:20][CH:21]=5)[N:13]=[N:12][N:11]=4)[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]23)=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 70604924HCID 70604924, compound

Product 1

HCID 70604553HCID 70604553, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 189 mg of 6-amino-2,2-dimethyl-3-(1-[4-benzyloxybenzyl]tetrazol-5-yl)penam in 4 ml of chloroform, is added, at ambient temperature, 0.038 ml of pyridine followed by 0.057 ml of phenylacetyl chloride. Stirring is continued for a further 45 minutes, and then the reaction mixture is diluted with 25 ml of chloroform and then washed with water. The organic phase is dried using anhydrous magnesium sulfate and then evaporated in vacuo. The residue is 209 mg (86% yield) of 6-(2-phenylacetamido)-2,2-dimethyl-3-(1-[4-benzyloxybenzyl]tetrazol-5-yl)penam. The NMR spectrum (in CDCl3) shows absorptions at 7.50-6.70 ppm (multiplet, aromatic hydrogens), 6.4 ppm (doublet, amide hydrogen), 5.80-5.20 ppm (multiplet, benzyl hydrogens and C-5 and C-6 hydrogens), 5.10 ppm (singlet, C-3 hydrogen), 5.05 ppm (singlet, benzyl hydrogens), 3.60 ppm (singlet, phenylacetyl methylene hydrogens), 1.30 ppm (singlet, C-2 methyl hydrogens) and 0.85 ppm (singlet, C-2 methyl hydrogens).

Workup

  1. washwashed with water
  2. customThe organic phase is dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-7c3a5539230b45eb84b6f2c5ac0ecc2a
Source dataset
uspto-grants-1978_09
Patent number
US04115385

Reaction notes

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