Water → HCID 178514550, 화합물

HRID 1111789

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HRID 1111789 반응식
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH:9]([S:14][C:15]3[NH:19][N:18]=[N:17][N:16]=3)[CH2:10][C:11]([OH:13])=[O:12])[CH2:7][S:8][C@H:3]12.O.CN1CCOCC1.[N:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][C:44](Cl)=[O:45])=[N+:34]=[N-:35]>CC(C)=O>[N:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][C:44]([NH:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH:9]([S:14][C:15]3[NH:16][N:17]=[N:18][N:19]=3)[CH2:10][C:11]([OH:13])=[O:12])[CH2:7][S:8][C@H:3]12)=[O:45])=[N+:34]=[N-:35]

참가 물질

6

반응물 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 227677832-Azidomethylphenylacetyl ChlorideHCID 178508097HCID 178508097, 화합물

생성물 1

HCID 178514550HCID 178514550, 화합물

시약·촉매·용매 1

HCID 180Acetone용매2회

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온도
0 °C

실험 절차

7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (3 g., 0.008 mole) was suspended in 50 ml. of water. The suspension was cooled to 0° C. and then N-methylmorpholine (3 g., 0.03 mole) was added. After a solution was obtained, 50 ml. of acetone was added. An acetone solution of 2-azidomethylphenylacetyl chloride (prepared from 2 g. of 2-azidomethylphenyl acetic acid and 2 ml. of thionyl chloride in 100 ml. of methylene chloride) was added dropwise at 0° to 5° C. over 10 minutes. The resulting mixture was stirred for one hour and then the acetone was distilled off with the aid of vacuum. The aqueous layer was extracted once with 50 ml. of toluene. To the aqueous layer was added 50 ml. of ethyl acetate and the pH was adjusted to 2.6 using phosphoric acid (85% diluted with equal volume of water). The ethyl acetate layer was carbon treated and dried over anhydrous sodium sulfate. After filtration the solution was concentrated to give 7-(2-azidomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-caboxylic acid as a foam-like product which weighed 3.6 g. NMR and IR spectroscopy data were consistent with the expected structure. A small sample was hydrogenated in water using Raney nickel as catalyst to give a product which was identical in every way to an authentic sample of 7-(2-aminomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (III).

후처리

  1. customAfter a solution was obtained
  2. distillationthe acetone was distilled off with the aid of vacuum
  3. extractionThe aqueous layer was extracted once with 50 ml
  4. additionTo the aqueous layer was added 50 ml
  5. additiontreated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration the solution
  8. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-1e76250c4ad64ab5ab0f5f4d1e404869
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04118563

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