Sodium Bicarbonate → HCID 131712876, compound

HRID 2199026Notes

Reaction equation

HRID 2199026 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][S:12][C:13]1[CH2:14][C@@H:15]2[CH:32]([CH:33]([O:35][C:36](=[O:38])[CH3:37])[CH3:34])[C:31](=[O:39])[N:16]2[C:17]=1[C:18]([O:20]CC1C=CC([N+]([O-])=O)=CC=1)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+:44]>O1CCOCC1.C(O)C.O.[Pd]>[CH2:1]([O:8][C:9]([CH2:11][S:12][C:13]1[CH2:14][C@@H:15]2[CH:32]([CH:33]([O:35][C:36](=[O:38])[CH3:37])[CH3:34])[C:31](=[O:39])[N:16]2[C:17]=1[C:18]([O-:20])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+:44]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 131712878HCID 131712878, compound

Product 1

HCID 131712876HCID 131712876, compound

Reagents, catalysts & solvents 4

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

Procedure

A solution of p-nitrobenzyl 2-benzyloxycarbonylmethylthio-6-(1-acetoxy)ethyl-carbapen-2-em-3-carboxylate (5.6 mg, 0.01 mmol) in dioxane (0.60 ml) is diluted with ethanol (0.05 ml) and water (0.35 ml) containing sodium bicarbonate (1.0 mg, 0.012 mmol). The solution is treated with 10% palladium on charcoal (5.5 mg) and hydrogenated at 40 psi for 30 minutes. The mixture is diluted with water (3 ml) and centrifuged to remove the catalyst which is washed with more water (2×1 ml). The combined aqueous supernatant is washed with ethyl acetate (4×2 ml), filtered through a cotton plug, concentrated in vacuo to ca. 1 ml, and lyophilized to yield the title compound as an amorphous solid: UV (0.1 M pH 7 phosphate buffer) 299 nm; NMR (D2O) δ1.30 (d, 3, J=6.7, CH3), 2.13 (s, 3, COCH3), 2.81 (dd, 1, J=9 and 18, H1a), 3.05 (dd, 1, J=10 and 18, H1b), 3.31 (dd, 1, J=3 and 5, H6), ~3.7(m, SCH2, obscured by impurities), 4.07 (m, 1, H5), 5.21 (m, 1, CHCH3), 5.27(s, 2, CH2 φ) and 7.48 (s, 5, C6H5); electrophoresis in 0.05 M pH 6.9 buffer at 2 KV for 20 minutes gives a single bioactive zone moving 3-5 cm toward the anode; HPLC on a C18Bondapak Reverse phase column using 10% THF/H2O at 1.0 ml/min gives a UV visible peak at retention time 17.4 mins (4.8 mins for thienamycin).

Workup

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

Sources & evidence

ORD record
ord-517b7da462fa438686a8f2bcc69d4287
Source dataset
uspto-grants-1982_11
Patent number
US04361512

Reaction notes

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