HCID 10723809, compound → HCID 9954958, compound

HRID 480388Notes

Reaction equation

HRID 480388 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:53])[C:7]([S:25][C@@H:26]1[CH2:30][CH2:29][O:28][C@@H:27]1[CH2:31][NH:32][C:33](=[O:52])[C@@H:34]([NH:38]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)[CH:35]([CH3:37])[CH3:36])=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].[H][H]>[Pd].[OH-].[Pd+2].[OH-].[Pt]=O.O>[NH2:38][C@@H:34]([CH:35]([CH3:37])[CH3:36])[C:33]([NH:32][CH2:31][C@@H:27]1[C@H:26]([S:25][C:7]2[C@H:6]([CH3:53])[C@H:5]3[N:9]([C:10](=[O:11])[C@@H:4]3[C@H:2]([OH:1])[CH3:3])[C:8]=2[C:12]([OH:14])=[O:13])[CH2:30][CH2:29][O:28]1)=[O:52]

Participants

7

Reactant 2

HCID 10723809HCID 10723809, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 9954958HCID 9954958, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

The 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-{[(2R,3R)-2-({[(2S)-3-methyl-2-({[(4-nitrobenzyl)oxy]carbonyl}amino)butanoyl]amino}methyl)tetrahydrofuran-3-yl]thio}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 1 is added to the biphasic solvent system of water and organic solvent in the presence of catalyst, without the addition of an acid acceptor. Suitable catalysts include palladium-on-carbon, palladium hydroxide, platinum oxide and the like. The reaction mixture is hydrogenated by shaking in a Parr hydrogenation apparatus under hydrogen pressure, until the reaction has reached completion as shown by monitoring the progress of the reaction by analytical high pressure liquid chromatography (HPLC) and cessation of hydrogen uptake. Suitably, the reaction is maintained at 20 to 30° C. for a preferred period of about 4 hours to about 24 hours at a hydrogen pressure of about 50-60 pounds-per-square inch (psi). The water portion and organic solvent portion are separated and the (4R, 5S, 6S)-3-[[(2R,3R)-2-[[[(S)-2-amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-6-[(R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 2 isolated from the water portion by lyophilization or reverse osmosis.

Workup

  1. customThe water portion and organic solvent portion are separated

Sources & evidence

ORD record
ord-3d6848bfce7740a4bbdca9ade7e16c00
Source dataset
uspto-grants-2003_11
Patent number
US06649756B2

Reaction notes

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