1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(2-[3-Azidomethyl-2-thienyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 614149Notes

Reaction equation

HRID 614149 reaction equation
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[NH:14][N:13]=[N:12][N:11]=3)[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.[N:17]([CH2:20][C:21]1[CH:25]=[CH:24][S:23][C:22]=1[CH2:26][C:27](O)=[O:28])=[N+:18]=[N-:19].Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.O>[N:17]([CH2:20][C:21]1[CH:25]=[CH:24][S:23][C:22]=1[CH2:26][C:27]([NH:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[NH:11][N:12]=[N:13][N:14]=3)[C:6]([CH3:8])([CH3:9])[S:7][C@H:3]12)=[O:28])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 203113693-Azidomethyl-2-thienylacetic AcidHCID 178431949HCID 178431949, compound

Product 1

HCID 1784319296-(2-[3-Azidomethyl-2-thienyl]acetamido)-2,2-dimethyl-3-(5-tetrazolyl)penamYield 88%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 5.48 g. (0.0228 mole) of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam in 200 ml. of 1:1 tetrahydrofuran-water is adjusted to pH 7.5, and then 4.5 g. (0.0228 mole) of 2-(3-azidomethyl-2-thienyl)acetic acid is added. The mixture is cooled to 0°-5° C., and 4.37 g. (0.0288 mole) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride is added. The reaction mixture is stirred at pH 6 and at 0°-5° C. for 2.5 hours. At this point, the tetrahydrofuran is removed by evaporation in vacuo and the pH is adjusted to 7.5. The aqueous residue is washed with ethyl acetate and then the pH is lowered to 2.2. The product is extracted into ethyl acetate. The ethyl acetate is dried and evaporated in vacuo. This affords 8.1 g. (88% yield) of the title compound as a foam. IR (KBr disc): 2100, 1800, 1666, 1529 and 1250 cm -1. NMR (CDCl3): 7.3 (d, 1H), 7.0 (d, 1H), 5.7 (m, 2H), 5.3 (s, 1H), 4.4 (s, 2H), 3.9 (s, 2H), 1.6 (s, 3H) and 1.1 ppm (s, 3H).

Workup

  1. temperatureThe mixture is cooled to 0°-5° C.
  2. customAt this point, the tetrahydrofuran is removed by evaporation in vacuo
  3. washThe aqueous residue is washed with ethyl acetate
  4. extractionThe product is extracted into ethyl acetate
  5. dry with materialThe ethyl acetate is dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-78538731d3054c05987ccf315c21ca98
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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