Sodium Azide → 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-3-carboxylic acid

HRID 263937

反応式

HRID 263937 の反応式
CC([O:4][CH2:5][C:6]1[CH2:23][S:22][C@@H:9]2[C@H:10](NC(CC3SC=CC=3)=O)[C:11](=O)[N:8]2[C:7]=1C([O-])=O)=O.[Na+].C(=O)(O)[O-:29].[Na+].[N-]=[N+]=[N-].[Na+]>O>[N:8]12[CH2:11][CH2:10][CH:9]1[S:22][CH2:23][C:6]([C:5]([OH:4])=[O:29])=[CH:7]2

参加物

5

反応物 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 23675321Cephalothin Sodium

生成物 1

HCID 1317200405-Thia-1-azabicyclo[4.2.0]oct-2-ene-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
37 fahrenheit

実験手順

A solution of commercial cephalothin sodium salt (5.0 g), sodium bicarbonate (1.06 g), sodium azide (0.82 g) and water (75 ml) is heated at approximately 50° C. (122° F.) until TLC (thin layer chromatography) shows the starting material is consumed. The reaction is cooled to approximately 3° C. (37° F.), covered with ethyl acetate and acidified with 1N HC1. The ethyl acetate extract is dried over Na2SO4, filtered and the filtrate is concentrated to dryness to give [6R[6a,7B]]-3-(azidomethyl)-8-oxo-7-](2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-3-carboxylic acid. A mixture of this azido intermediate (1.0 g), 10% Pd/C (1.0 g), NaHCO3 (1.54 g) and 75% methanol/H2O is subjected to hydrogenation at room temperature until TLC shows the disappearance of starting azide. The catalyst is removed by filtration and the filtrate is concentrated to dryness. The residue is dissolved in water, acidified with 1N HCl and the solution is washed with CHCl3. The aqueous phase is concentrated to dryness and the crude product is purified using 50W-X4 cation exchange resin to give product (II).

後処理

  1. customis consumed
  2. extractionThe ethyl acetate extract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated to dryness

出典と根拠

ORDレコード
ord-8ac19ee89413497a9b69490cee86b13c
出典データセット
uspto-grants-1997_07
特許番号
US05646139

関連ノート

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