2,3-Dihydrofuran → p-nitrobenzyl (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[4-(2-hydroxyethyl)-1,2,3-triazol-1-yl]carbapen-2-em-3-carboxylate

HRID 329682Notes

Reaction equation

HRID 329682 reaction equation
[N:1]([C:4]1[CH2:5][C@@H:6]2[C@@H:23]([C@H:24]([OH:26])[CH3:25])[C:22](=[O:27])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10])=[N+:2]=[N-:3].[O:28]1[CH:32]=[CH:31][CH2:30][CH2:29]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:26][C@@H:24]([C@H:23]1[C:22](=[O:27])[N:7]2[C:8]([C:9]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)=[O:10])=[C:4]([N:1]3[CH:32]=[C:31]([CH2:30][CH2:29][OH:28])[N:3]=[N:2]3)[CH2:5][C@H:6]12)[CH3:25]

Participants

5

Reactant 3

HCID 709342,3-DihydrofuranHCID 516892Sodium BicarbonateHCID 14329106p-nitrobenzyl (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]-carbapen-2-em-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of p-nitrobenzyl (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]-carbapen-2-em-3-carboxylate (75 mg, 0.2 mmol) and 2,3-dihydrofuran (0.25 ml) in anhydrous tetrahydrofuran (5 ml) containing excess sodium bicarbonate is kept at 4° C. for 1 week. The mixture is filtered and the filtrate evaporated under vacuum. The residue is purified by preparative thin layer chromatography on silica gel to afford p-nitrobenzyl (5R,6S)-6-[(R)-1-hydroxyethyl]-2-[4-(2-hydroxyethyl)-1,2,3-triazol-1-yl]carbapen-2-em-3-carboxylate.

Workup

  1. waitis kept at 4° C. for 1 week
  2. filtrationThe mixture is filtered
  3. customthe filtrate evaporated under vacuum
  4. customThe residue is purified by preparative thin layer chromatography on silica gel

Sources & evidence

ORD record
ord-7e6f2a4c2e42491ea4eeb3bf486701e5
Source dataset
uspto-grants-1990_01
Patent number
US04892869

Reaction notes

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