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

反応式

HRID 329931 の反応式
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]

参加物

5

反応物 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 5742673Cefotaxime

生成物 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

試薬・触媒・溶媒 1

HCID 1061Phosphate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1ba60b76e224457e8cb6cfb48b57b952
出典データセット
uspto-grants-1990_01
特許番号
US04894371

関連ノート

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