Cephalothin → HCID 70636083、化合物

HRID 1414679ノート

反応式

HRID 1414679 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:27][CH3:28])[C:25](=[O:26])[N:12]2[C:13]([C:22]([OH:24])=[O:23])=[C:14]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:15][S:16][C@H:11]12)=[O:8].CC(OCC1CS[C@@H]2[C@H](NC(CC3SC=CC=3)=O)C(=O)N2C=1C(O)=O)=O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:27][CH3:28])[C:25](=[O:26])[N:12]2[CH:13]([C:22]([OH:24])=[O:23])[C:14]([CH2:17][O:18][C:19](=[O:21])[CH3:20])=[CH:15][S:16][C@H:11]12)=[O:8]

参加物

5

反応物 3

HCID 6024CephalothinHCID 7918Acetic AnhydrideHCID 64521823-[(Acetyloxy)methyl]-7-{[1-hydroxy-2-(thiophen-2-yl)ethylidene]amino}-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

生成物 1

HCID 70636083HCID 70636083、化合物収率 68.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a cooled (0°), stirred solution of 7.75 g. of 7-(2-thienylacetamido)-7-methoxy-3-acetoxymethyl- 3-cephem-4-carboxylic acid [prepared from cephalothin in accordance with procedures described by G. A. Koppel and and R. E. Koehler, J. Amer. Chem. Soc., 95, 2403 (1973 )]in 46 ml. of dry pyridine was added 5.02 ml. of acetic anhydride. The reaction mixture was allowed to stir with cooling for 2 hours, after which time the mixture was evaporated in vacuo to near dryness. The residue was dissolved in ethyl acetate, and the resulting solution was extracted 3 times with aqueous sodium bicarbonate. The aqueous extracts were combined, layered with ethyl acetate, and acidified with cold 1N.HCl. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided 5.29 g. (68.2 percent) of the title product as a browh froth. Thin layer chromatography of the methyl ester derived from diazomethane exhibited a single spot. For identification purposes a small portion of the product acid was also converted to the corresponding benzhydryl ester using diphenyldiazomethane. Chromatography on a small silica gel column provided pure benzhydryl 7-(2-thienylacetamido)-7 -methoxy-3-acetoxymethyl-2-cephem-4-carboxylate: ir (CHCl3) 1780 cm-1 (β-lactam); nmr (CDCl3) δ1.92 (s, 3, OAc), 3.42 (s, 3, OCH3), 3.85 (s, 2, side chain CH2), 4.55 (s, 2, --CH2OAc), 5.01 (m, 1, C4 --H), 5.35 (s, 1, C6 --H) and 6.35 (m, 6, C2H).

後処理

  1. temperatureTo a cooled (0°)
  2. stirringto stir
  3. temperaturewith cooling for 2 hours
  4. customafter which time the mixture was evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionthe resulting solution was extracted 3 times with aqueous sodium bicarbonate
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customEvaporation in vacuo to dryness
  11. customprovided 5.29 g

出典と根拠

ORDレコード
ord-dd6e08a1b0544b3d91b33b6796665119
出典データセット
uspto-grants-1977_01
特許番号
US04001226

反応ノート

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