Reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[N:6][N:7]([C:9]2[CH2:10][C@@H:11]3[CH2:28][C:27](=[O:29])[N:12]3[C:13]=2[C:14]([O:16]CC2C=CC([N+]([O-])=O)=CC=2)=[O:15])[CH:8]=1.N1(CCCS(O)(=O)=O)CCOCC1>O1CCOCC1.O.C(O)C.[Pd]>[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[N:6][N:7]([C:9]2[CH2:10][C@@H:11]3[CH2:28][C:27](=[O:29])[N:12]3[C:13]=2[C:14]([OH:16])=[O:15])[CH:8]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Procedure
A solution of p-nitrobenzyl 2-(4-[2-hydroxyethyl]-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylate (3.5 mg, 8.8 micromol) in dioxane (300 microliter), deionized water (180 microliter), absolute ethanol (24 microliter), and pH 7.0 4-morpholinepropanesulfonic acid buffer (60 microliter of 0.5M) was shaken with 10% (w/w) palladium on charcoal (7.0 mg) under hydrogen (50 psig) at ambient temperature. After 40 min. the mixture was centrifuged and the pellet washed with deionized water (3×0.5 ml). The combined supernate and washes were extracted with ethyl acetate (3×0.5 ml) and concentrated under vacuum to provide 0.5 ml of a solution of 2-(4-[2hydroxyethyl]-1,2,3-triazol-1-yl)-carbapen-2-em-3-carboxylic acid, UV λmax 299 nm which quenched upon addition of hydroxylamine hydrochloride and dipotassium hydrogen phosphate.
Workup
- washthe pellet washed with deionized water (3×0.5 ml)
- extractionThe combined supernate and washes were extracted with ethyl acetate (3×0.5 ml)
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-c0e41c04accb4c17b5c9fae0c235599f
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05140030
Linked notes
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