Sodium Iodide → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 329931

반응식

HRID 329931 반응식
CC(O[CH2:5][C:6]1[CH2:27][S:26][C@@H:9]2[C@H:10]([NH:13][C:14](/[C:16](/[C:20]3[N:24]=[C:23]([NH2:25])[S:22][CH:21]=3)=[N:17]\[O:18][CH3:19])=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:28]([OH:30])=[O:29])=O.[N-:31]=[N+:32]=[N-:33].[Na+].[I-].[Na+]>P([O-])([O-])([O-])=O>[N:31]([CH2:5][C:6]1[CH2:27][S:26][C@@H:9]2[CH:10]([NH:13][C:14](=[O:15])/[C:16](/[C:20]3[N:24]=[C:23]([NH2:25])[S:22][CH:21]=3)=[N:17]\[O:18][CH3:19])[C:11](=[O:12])[N:8]2[C:7]=1[C:28]([OH:30])=[O:29])=[N+:32]=[N-:33]

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 5742673Cefotaxime

생성물 1

HCID 141548216(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

시약·촉매·용매 1

HCID 1061Phosphate용매

실험 절차

To a solution of cefotaxime (5.24 g.) in phosphate buffer (pH 6.4, 440 ml.) was added sodium azide (2.86 g.) and sodium iodide (1.65 g.) and the mixture was immersed in a 70° bath with stirring for 4.5 hours. The solvent was evaporated to the point of precipitation and then the pH adjusted to 2.5 with 2N aqueous HCl. The resulting precipitate was collected, washed with water, acetone and ether and dried over P2O5 to give 3-azidomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid in quantative yield, having the following n.m.r. in solvent A:--3.4 (d, 1 H); 3.7 (d, 1 H); 3.86 (s, 3 H); 3.95 (d, 1 H); 4.4 (d, 1 H); 5.15 (d, 1 H); 5.78 (d, 1 H); 6.75 (s, 1 H).

후처리

  1. customwas immersed in a 70°
  2. customThe solvent was evaporated to the point of precipitation
  3. customThe resulting precipitate was collected
  4. washwashed with water, acetone and ether
  5. dry with materialdried over P2O5

출처 및 근거

ORD 기록
ord-1ba60b76e224457e8cb6cfb48b57b952
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894371

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