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

HRID 1290366Notes

Reaction equation

HRID 1290366 reaction equation
[N+](C1C=CC(C[O:11][C:12]([C:14]2[N:15]3[CH:18]([CH:19]([CH3:31])[C:20]=2[S:21][CH:22]2[CH2:26][CH:25]([CH2:27][N:28]=[N+]=[N-])[O:24][CH2:23]2)[CH:17]([CH:32]([OH:34])[CH3:33])[C:16]3=[O:35])=[O:13])=CC=1)([O-])=O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[Pd].O1CCOCC1>[NH2:28][CH2:27][CH:25]1[O:24][CH2:23][CH:22]([S:21][C:20]2[CH:19]([CH3:31])[CH:18]3[N:15]([C:16](=[O:35])[CH:17]3[CH:32]([OH:34])[CH3:33])[C:14]=2[C:12]([OH:13])=[O:11])[CH2:26]1

Participants

5

Reactant 2

HCID 24243Trisodium PhosphateHCID 867503233-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-6-(1-Hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Product 1

HCID 749715283-[[5-(Aminomethyl)tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidYield 29.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound is prepared by the procedure of Example 18 using 2.8 g of product from Example 45, 0.60 g of 10% palladium/carbon, 27 ml of sodium phosphate buffer (pH 7) and 82 ml of dioxane to give 0.562 g of the desired product.

Sources & evidence

ORD record
ord-2d196633755f4090bb3d9b2df64baabb
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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