Sodium Bicarbonate → HCID 131712882, compound

HRID 2199028Notes

Reaction equation

HRID 2199028 reaction equation
[N+](C1C=CC(C[O:9][C:10]([CH2:12][S:13][C:14]2[CH2:15][C@@H:16]3[CH:33]([CH:34]([OH:36])[CH3:35])[C:32](=[O:37])[N:17]3[C:18]=2[C:19]([O:21]CC2C=CC([N+]([O-])=O)=CC=2)=[O:20])=[O:11])=CC=1)([O-])=O.C(=O)(O)[O-].[Na+:44]>O1CCOCC1.C(O)C.O.[Pd]>[C:10]([CH2:12][S:13][C:14]1[CH2:15][C@@H:16]2[CH:33]([CH:34]([OH:36])[CH3:35])[C:32](=[O:37])[N:17]2[C:18]=1[C:19]([O-:21])=[O:20])([OH:11])=[O:9].[Na+:44].[Na+:44].[C:10]([CH2:12][S:13][C:14]1[CH2:15][C@@H:16]2[CH:33]([CH:34]([OH:36])[CH3:35])[C:32](=[O:37])[N:17]2[C:18]=1[C:19]([O-:21])=[O:20])([OH:11])=[O:9]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 131712884HCID 131712884, compound

Product 1

HCID 131712882HCID 131712882, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of crude p-nitrobenzyl 2-(p-nitrobenzyloxycarbonyl)methylthio-6-(1-hydroxy)ethyl-carbapen-2-em-3-carboxylate (8.7 mg) in dioxane (1.20 ml) is diluted with ethanol (0.10 ml) and water (0.70 ml) containing sodium bicarbonate (2.3 mg). The resulting solution is treated with 10% palladium on charcoal (15 mg) and hydrogenated at 40 psi for 60 minutes. The mixture is diluted with water to 5 ml and centrifuged to remove the catalyst which is washed with more water (2×1 ml). The combined aqueous solution is washed with ethyl acetate (4×3 ml), filtered through a cotton plug, concentrated in vacuo to ca. 1 ml, and lyophilized to provide the title compound as a solid: UV (pH 7 phosphate buffer) 301 nm; electrophoresis (0.05 M pH 7 phosphate buffer 2 KV, 20 ma, 20 mins) gives a biactive zone migrating 9.3 cm toward the anode (dicarboxylate).

Workup

  1. customto remove the catalyst which
  2. washis washed with more water (2×1 ml)
  3. washThe combined aqueous solution is washed with ethyl acetate (4×3 ml)
  4. filtrationfiltered through a cotton plug
  5. concentrationconcentrated in vacuo to ca. 1 ml

Sources & evidence

ORD record
ord-74a504ad94d74893b295f425cbcd2722
Source dataset
uspto-grants-1982_11
Patent number
US04361512

Reaction notes

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