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

HRID 265248

반응식

HRID 265248 반응식
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

참가 물질

5

반응물 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 23675321Cephalothin Sodium

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
37 fahrenheit

실험 절차

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 HCl. 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).

후처리

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

출처 및 근거

ORD 기록
ord-25e596dafd8c412abeae798a8528ac4c
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648346

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