Sodium Bicarbonate → HCID 101934793, compound

HRID 1825338Notes

Reaction equation

HRID 1825338 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:35](=[O:36])[N:6]2[C:7]([C:22]([O:24]CC3C=CC([N+]([O-])=O)=CC=3)=[O:23])=[C:8]([C:10]3[CH:14]=[C:13]([CH3:15])[N:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:11]=3)[CH2:9][C@H:5]12)[CH3:3].C(=O)([O-])O.[Na+:41]>O1CCCC1.O.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:35](=[O:36])[N:6]2[C:7]([C:22]([O-:24])=[O:23])=[C:8]([C:10]3[CH:14]=[C:13]([CH3:15])[N:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:11]=3)[CH2:9][C@H:5]12)[CH3:3].[Na+:41]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 10696349HCID 10696349, compound

Product 1

HCID 101934793HCID 101934793, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-(5-methyl-1-phenylpyrazol-3-yl)carbapen-2-em-3-carboxylate (122 mg) in tetrahydrofuran (THF) (10 ml) and water (10 ml) was treated with sodium hydrogen carbonate (42 mg) (10 ml) and 3% Pd—C catalyst (50 mg) and the mixture was hydrogenated at atmospheric pressure for 5-10 min. The mixture was filtered through Kieselguhr, washing the filter cake with water and ethyl acetate. Combined filtrate and washings were reduced in volume using a rotary evaporator, a little NaCl was added and the mixture was chromatographed on a Diaion HP20SS column (2×10 cm), eluting with water (200 ml), followed by water/THF mixtures: 2% THF (10 ml); followed by 3% THF (100 ml), followed by 4% THF, followed by 6% THF. Fractions were monitored by uv and hplc. Fractions containing the product were combined and evaporated to lower volume and then freeze-dried to give sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-(5-methyl-1-phenylpyrazol-3-yl)carbapen-2-em-3-carboxylate (80 mg) νmax(KBr)/cm−1 1786, 1756, 1588, 1501, 1412, 1383, 1359, 1288 1246, 1223, and 1145; λmax(H2O)/nm 300.0 (ε/dm3 mol−1 cm−1 13,232), 236.5 (ε 7,027); δ(D2O) 1.26 (3H, d, J 6.4 Hz), 2.20 (3H,s), 3.1-3.29 (2H, m), 3.46 (1H, dd, J 2.9 & 5.9 Hz), 4.16-4.28 (2H, m), 6.61 (1H,s), 7.39-7.57 (5H,m).

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. washwashing the filter cake with water and ethyl acetate
  3. customa rotary evaporator
  4. additiona little NaCl was added
  5. customthe mixture was chromatographed on a Diaion HP20SS column (2×10 cm)
  6. washeluting with water (200 ml)
  7. additionFractions containing the product
  8. customevaporated
  9. customfreeze-dried

Sources & evidence

ORD record
ord-0bdc376be0094644a270dbb3ca00acc1
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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