Sodium Bicarbonate → sodium (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[4-(2-hydroxy ethyl)-1,2,3-triazol-1-yl]carbapen-2-em-3-carboxylate

HRID 1762686Notes

Reaction equation

HRID 1762686 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([O:20]CC3C=CC([N+]([O-])=O)=CC=3)=[O:19])=[C:8]([N:10]3[CH:14]=[C:13]([CH2:15][CH2:16][OH:17])[N:12]=[N:11]3)[CH2:9][C@H:5]12)[CH3:3].C(=O)(O)[O-].[Na+:37]>O1CCCC1.C(O)C.O.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([O-:20])=[O:19])=[C:8]([N:10]3[CH:14]=[C:13]([CH2:15][CH2:16][OH:17])[N:12]=[N:11]3)[CH2:9][C@H:5]12)[CH3:3].[Na+:37]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 14329122p-nitrobenzyl (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[4-(2-hydroxyethyl)-1,2,3-triazol-1-yl]carbapen-2-em-3-carboxylate

Product 1

HCID 23718249sodium (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[4-(2-hydroxy ethyl)-1,2,3-triazol-1-yl]carbapen-2-em-3-carboxylate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-nitrobenzyl (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[4-(2-hydroxyethyl)-1,2,3-triazol-1-yl]carbapen-2-em-3-carboxylate (35 mg, 0.08 mmol) in tetrahydrofuran (5.5 ml) is diluted with ethanol (2.8 ml) and DI water (4.2 ml) containing sodium bicarbonate (6.8 mg, 0.08 mmol). The resulting solution is added to a prereduced mixture of 10% palladium on carbon (37 mg) in ethanol (2.7 ml), and the mixture is stirred under an atmosphere of hydrogen for 2 hours at ambient temperature. The mixture is filtered through a celite pad which is washed with water. The filtrate and wash are extracted with methylene chloride and diethyl ether, concentrated under vacuum, and lyophilized to afford sodium (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[4-(2-hydroxyethyl)-1,2,3-triazol-1-yl]carbapen-2-em-3-carboxylate.

Workup

  1. filtrationThe mixture is filtered through a celite pad which
  2. washis washed with water
  3. washThe filtrate and wash
  4. extractionare extracted with methylene chloride and diethyl ether
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fceec2574d764327a9c69bcb4bdb16d9
Source dataset
uspto-grants-1989_05
Patent number
US04833167

Reaction notes

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