Trisodium Phosphate → 3-[[5-[[[(Dimethylamino)methylene]amino]methyl]tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 54793

Reaction equation

HRID 54793 reaction equation
P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[N:9]([CH2:12][CH:13]1[O:17][CH2:16][CH:15]([S:18][C:19]2[CH:25]([CH3:26])[CH:24]3[N:21]([C:22](=[O:30])[CH:23]3[CH:27]([OH:29])[CH3:28])[C:20]=2[C:31]([OH:33])=[O:32])[CH2:14]1)=[N+]=[N-].C(O[CH:38](OC(C)C)[N:39]([CH3:41])[CH3:40])(C)C>>[CH3:38][N:39]([CH:41]=[N:9][CH2:12][CH:13]1[O:17][CH2:16][CH:15]([S:18][C:19]2[CH:25]([CH3:26])[CH:24]3[N:21]([C:22](=[O:30])[CH:23]3[CH:27]([OH:29])[CH3:28])[C:20]=2[C:31]([OH:33])=[O:32])[CH2:14]1)[CH3:40]

Participants

4

Reactant 3

HCID 24243Trisodium PhosphateHCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amineHCID 867507523-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Product 1

HCID 749989133-[[5-[[[(Dimethylamino)methylene]amino]methyl]tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Conditions

Temperature
0 °C

Procedure

Three ml of sodium phosphate buffer, pH 7, is cooled to 0° C. and 0.052 g of product from Example 46 is added. To this cooled solution is added, dropwise, 159 μl of N,N-dimethylformamide diisopropyl acetal, while maintaining the pH below 8.5. The reaction mixture is stirred at 0° C. for 35 minutes, pH adjusted to 7.0 and freeze-dried. The residue is purified by chromato- graphy (C18 reverse phase tlc plates: 75% aqueous ethyl alcohol) to give 0.031 g of the desired product.

Workup

  1. additionTo this cooled solution is added
  2. customfreeze-dried
  3. customThe residue is purified by chromato- graphy (C18 reverse phase tlc plates: 75% aqueous ethyl alcohol)

Sources & evidence

ORD record
ord-bc1cd41adae64bb3ab7f17bd494c1e01
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Linked notes

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