HCID 13470801, compound → HCID 178514122, compound

HRID 482840Notes

Reaction equation

HRID 482840 reaction equation
[Na+:1].[NH2:2][C:3]1[S:4][CH:5]=[C:6](/[C:8](=[N:26]/[O:27][CH2:28][C:29]([O:31]CC2C=CC([N+]([O-])=O)=CC=2)=[O:30])/[C:9]([NH:11][C@H:12]2[C@@H:15]([CH2:16][O:17][C:18](=[O:20])[NH2:19])[N:14]([S:21]([O-:24])(=[O:23])=[O:22])[C:13]2=[O:25])=[O:10])[N:7]=1>CO.[Pd]>[Na+:1].[NH2:2][C:3]1[S:4][CH:5]=[C:6](/[C:8](=[N:26]/[O:27][CH2:28][C:29]([OH:31])=[O:30])/[C:9]([NH:11][C@H:12]2[C@@H:15]([CH2:16][O:17][C:18](=[O:20])[NH2:19])[N:14]([S:21]([O-:24])(=[O:22])=[O:23])[C:13]2=[O:25])=[O:10])[N:7]=1

Participants

4

Reactant 1

HCID 13470801HCID 13470801, compound

Product 1

HCID 178514122HCID 178514122, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

270 mg (0.43 mmol) of (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(p-nitrobenzyloxycarbonyl)methoxyimino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid sodium salt are dissolved in 30 ml of methanol and hydrogenated over 5% palladium on infusorial earth (150 mg). The catalyst is filtered off and the solvent is evaporated. The residue is taken up in 2.5 ml of water and washed twice with ethyl acetate. The aqueous phase is chromatographed (reverse-phase, water as the elution agent). There are obtained 115 mg (54%) of (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid sodium salt.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is evaporated
  3. washwashed twice with ethyl acetate
  4. customThe aqueous phase is chromatographed (reverse-phase, water as the elution agent)

Sources & evidence

ORD record
ord-a65ceddb4b1a462d8b49361c2a58e642
Source dataset
uspto-grants-1986_03
Patent number
US04576751

Reaction notes

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