HCID 15058102, compound → HCID 23706512, compound

HRID 1906607Notes

Reaction equation

HRID 1906607 reaction equation
[Na+:1].[NH2:2][C:3]1[S:4][CH:5]=[C:6](/[C:8](=[N:22]/[O:23][C:24]([C:27]([O:29]CC2C=CC([N+]([O-])=O)=CC=2)=[O:28])([CH3:26])[CH3:25])/[C:9]([NH:11][C@H:12]2[C@@H:15]([CH3:16])[N:14]([S:17]([O-:20])(=[O:19])=[O:18])[C:13]2=[O:21])=[O:10])[N:7]=1>O.O1CCCC1.[Pd]>[Na+:1].[NH2:2][C:3]1[S:4][CH:5]=[C:6](/[C:8](=[N:22]/[O:23][C:24]([C:27]([OH:29])=[O:28])([CH3:25])[CH3:26])/[C:9]([NH:11][C@H:12]2[C@@H:15]([CH3:16])[N:14]([S:17]([O-:20])(=[O:19])=[O:18])[C:13]2=[O:21])=[O:10])[N:7]=1

Participants

4

Reactant 1

HCID 15058102HCID 15058102, compound

Product 1

HCID 23706512HCID 23706512, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

115 mg (0.19 mmol) of (3S,4R)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(p-nitro-benzyloxycarbonyl)-1-methylethoxy]imino]acetamido]-4-methyl-2-oxo-1-azetidinesulphonic acid sodium salt are dissolved in 40 ml of water/tetrahydrofuran (1:1) and the solution is hydrogenated for 12 hours over 300 ml of 10% palladium/carbon. The catalyst is filtered off and the solvent is evaporated under reduced pressure. The oil obtained is chromatographed (230-400 mesh, chloroform/methanol/n-propanol/water (4:6:1:4) as the solvent]. There are obtained 28.6 mg (33%) of (3S,4R)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(1-carboxy-1-methylethoxy]imino]acetamido]-4-methyl-2-oxo-1-azetidinesulphonic acid sodium salt.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is evaporated under reduced pressure
  3. customThe oil obtained
  4. customis chromatographed (230-400 mesh, chloroform/methanol/n-propanol/water (4:6:1:4) as the solvent]

Sources & evidence

ORD record
ord-4e5637ab0dd84856831d788fd7609720
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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