Triethylamine → 3-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1111752ノート

反応式

HRID 1111752 の反応式
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:15]([OH:17])=O)[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH3:18][C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][C@@H:26]2[C@H:27]([NH2:30])[C:28](=[O:29])[N:25]2[C:24]=1[C:33]([OH:35])=[O:34])=[O:20].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37]>C(Cl)Cl.C(O)CC>[CH2:36]([NH+:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37].[C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][CH:26]2[N:25]([C:28](=[O:29])[CH:27]2[NH2:30])[C:24]=1[C:33]([O-:35])=[O:34])(=[O:20])[CH3:18].[C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][CH:26]2[N:25]([C:28](=[O:29])[CH:27]2[NH:30][C:15](=[O:17])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:10][CH:9]=2)[C:12]([OH:14])=[O:13])[C:24]=1[C:33]([OH:35])=[O:34])(=[O:20])[CH3:18]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 4413287-Aminocephalosporanic acid2 回HCID 22767759p-Azidomethylphenylmalonic acid

生成物 2

HCID 227677693-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 1317101243-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid triethylammonium salt

試薬・触媒・溶媒 2

HCID 10311-Propanol溶媒HCID 6344Dichloromethane溶媒

実験手順

α-Carboxy-p-azidomethylphenylacetyl nitrophenyl polymer, prepared according to the procedure described in Canadian Pat. No. 892,580, carrying 4 m. mole of p-azidomethyl-phenylmalonic acid was suspended for 8 hours in 20 ml of dry methylene chloride solution containing 1 m. mole of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid triethylammonium salt, which is prepared from 544 mg of 7-aminocephalosporanic acid (1 m. mole) and 0.56 ml of triethylamine (1 m. mole) at room temperature. After only traces of 7-aminocephalosporanic acid remain in solution, which is determined by thin layer chromatography on cellulose in 70% aqueous propanol, the polymer was filtered off and washed with 3 portions of 5- ml each of methylene chloride. The combined filtrates were evaporated and the residue was dissolved in 20 ml of distilled water. This solution was acidified to pH 2 by adding 0.2 normal hydrochloric acid and extracted with ethyl acetate. The organic solution was dried over sodium sulfate and evaporated at room temperature. The remaining soldi was dried overnight over phosphorus pentoxide under vacuum to give 3-[ (acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

後処理

  1. customα-Carboxy-p-azidomethylphenylacetyl nitrophenyl polymer, prepared
  2. additioncontaining 1 m
  3. filtrationthe polymer was filtered off
  4. washwashed with 3 portions of 5- ml each of methylene chloride
  5. customThe combined filtrates were evaporated
  6. dissolutionthe residue was dissolved in 20 ml of distilled water
  7. additionby adding 0.2 normal hydrochloric acid
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic solution was dried over sodium sulfate
  10. customevaporated at room temperature
  11. dry with materialThe remaining soldi was dried overnight over phosphorus pentoxide under vacuum

出典と根拠

ORDレコード
ord-8ac4a81983a74569a8f599b6cf27ea20
出典データセット
uspto-grants-1978_10
特許番号
US04118562

反応ノート

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