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 → 6-(1-Hydroxyethyl)-4-methyl-7-oxo-3-[[tetrahydro-5-[[[(methylamino)acetyl]amino]methyl]-3-furanyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 1290369Notes

Reaction equation

HRID 1290369 reaction equation
[NH2:1][CH2:2][CH:3]1[O:7][CH2:6][CH:5]([S:8][C:9]2[CH:15]([CH3:16])[CH:14]3[N:11]([C:12](=[O:20])[CH:13]3[CH:17]([OH:19])[CH3:18])[C:10]=2[C:21]([OH:23])=[O:22])[CH2:4]1>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].CN1CC(=O)OC1=O.O1CCOCC1>[OH:19][CH:17]([CH:13]1[C:12](=[O:20])[N:11]2[CH:14]1[CH:15]([CH3:16])[C:9]([S:8][CH:5]1[CH2:4][CH:3]([CH2:2][NH:1][C:21](=[O:22])[CH2:10][NH:11][CH3:12])[O:7][CH2:6]1)=[C:10]2[C:21]([OH:23])=[O:22])[CH3:18]

Participants

5

Reactant 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 acid

Product 1

HCID 740859006-(1-Hydroxyethyl)-4-methyl-7-oxo-3-[[tetrahydro-5-[[[(methylamino)acetyl]amino]methyl]-3-furanyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidYield 87.7%

Reagents, catalysts & solvents 3

HCID 24243Trisodium PhosphateSolventHCID 312751,4-DioxaneSolventHCID 1386033-Methyloxazolidine-2,5-dioneSolvent

Procedure

The title compound is prepared by the procedure of Example 47 using 0.068 g of product from Example 46 in 2.0 ml of sodium phosphate buffer (pH 8.5) and 0.029 g of 3-methyl-2,5-oxazolidinedione, prepared by the procedure described in J. Org. Chem., 34, No. 1, 243(1969), in 1 ml of dioxane to give 0.036 g of the desired product.

Workup

  1. customprepared by the procedure

Sources & evidence

ORD record
ord-2ccd7173b4e346b9b7542de97054dec2
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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