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 1450319

Reaction equation

HRID 1450319 reaction equation
P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].[NH2:9][CH2:10][CH:11]1[O:15][CH2:14][CH:13]([S:16][C:17]2[CH:23]([CH3:24])[CH:22]3[N:19]([C:20](=[O:28])[CH:21]3[CH:25]([OH:27])[CH3:26])[C:18]=2[C:29]([OH:31])=[O:30])[CH2:12]1.C(O[CH:36](OC(C)C)[N:37]([CH3:39])[CH3:38])(C)C>>[CH3:36][N:37]([CH:39]=[N:9][CH2:10][CH:11]1[O:15][CH2:14][CH:13]([S:16][C:17]2[CH:23]([CH3:24])[CH:22]3[N:19]([C:20](=[O:28])[CH:21]3[CH:25]([OH:27])[CH3:26])[C:18]=2[C:29]([OH:31])=[O:30])[CH2:12]1)[CH3:38]

Participants

4

Reactant 3

HCID 24243Trisodium PhosphateHCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amineHCID 74971528HCID 74971528, compound

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-741084069e7d4342a6ff278c0e1c3b52
Source dataset
uspto-grants-1997_02
Patent number
US05602118

Linked notes

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