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 2118584Notes

Reaction equation

HRID 2118584 reaction equation
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]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 5742673Cefotaxime

Product 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

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

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, 1H); 3.7 (d, 1H); 3.86 (s, 3H); 3.95 (d, 1H); 4.4 (d, 1H); 5.15 (d, 1H); 5.78 (d, 1H); 6.75 (s, 1H).

Workup

  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

Sources & evidence

ORD record
ord-442f5d96a67a4567bbe554372c27da29
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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