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

HRID 614149ノート

反応式

HRID 614149 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-78538731d3054c05987ccf315c21ca98
出典データセット
uspto-grants-1979_03
特許番号
US04143039

反応ノート

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