HCID 13470801, compound → HCID 178514122, compound

HRID 1906605Notes

Reaction equation

HRID 1906605 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>[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

3

Reactant 1

HCID 13470801HCID 13470801, compound

Product 1

HCID 178514122HCID 178514122, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

270 mg (0.43 mmol) of (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid sodium salt are dissolved in 30 ml of methanaol and the solution is hydrogenated over 150 mg of 5% palladium-on-silica gel. 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 using water as the eluting 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

Sources & evidence

ORD record
ord-d1d4f3dac0924763bd23c41d0143d79a
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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