Water → 3-[[5-[[Acetyl(phenylmethoxy)amino]methyl]tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt

HRID 1290381Notes

Reaction equation

HRID 1290381 reaction equation
[N+](C1C=CC(C[O:11][C:12]([C:14]2[N:15]3[CH:18]([CH:19]([CH3:40])[C:20]=2[S:21][CH:22]2[CH2:26][CH:25]([CH2:27][N:28]([C:37](=[O:39])[CH3:38])[O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:24][CH2:23]2)[CH:17]([CH:41]([OH:43])[CH3:42])[C:16]3=[O:44])=[O:13])=CC=1)([O-])=O.C(=O)(O)[O-].[Na+:49].O>[Pd].O1CCOCC1>[Na+:49].[C:37]([N:28]([CH2:27][CH:25]1[O:24][CH2:23][CH:22]([S:21][C:20]2[CH:19]([CH3:40])[CH:18]3[N:15]([C:16](=[O:44])[CH:17]3[CH:41]([OH:43])[CH3:42])[C:14]=2[C:12]([O-:13])=[O:11])[CH2:26]1)[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 1317198443-[[5-[[Acetyl(phenylmethoxy)amino]methyl]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 1317198433-[[5-[[Acetyl(phenylmethoxy)amino]methyl]tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium saltYield 26.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound is prepared by the procedure of Example 18 using 0.272 g of product from Example 74, 0.0402 g of sodium bicarbonate, 2 ml of water, 11.3 ml of dioxane, and 0.110 g of 10% palladium/carbon to give 0.059 g of the desired product.

Sources & evidence

ORD record
ord-e157633f4ff541aeb9dc34158d9eef4d
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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