HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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 847212
Notes
Print preview

Reaction equation

HRID 847212 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938PalladiumCatalyst
HCID 702
Ethanol
Solvent
2×
HCID 962WaterSolvent
HCID 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-8d4d8a16624248579d7d9a704aa79ac6
Source dataset
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05140030

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes