MeOH tetrahydrofuran → HCID 70620351, compound

HRID 1679194Notes

Reaction equation

HRID 1679194 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:22]([O:24]CC3C=CC([N+]([O-])=O)=CC=3)=[O:23])=[C:14]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:15][S:16][C@:11]12[O:37][CH3:38])=[O:8].C1COCC1.CO>CCOC(C)=O.[Pd]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:22]([OH:24])=[O:23])=[C:14]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:15][S:16][C@:11]12[O:37][CH3:38])=[O:8]

Participants

5

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 70620182HCID 70620182, compound

Product 1

HCID 70620351HCID 70620351, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5% Pd on charcoal (120 mg., prereduced in 1:1 THF-MeOH), the major isomer of p-nitrobenzyl 7-(2-thienylacetamido)-6-methoxy-3-acetoxymethyl-ceph-3-em-4-carboxylate (60 mg.), and 1:1 THF-MeOH (3 ml.) is hydrogenated at atmospheric pressure and room temperature for 3 hrs. The mixture is filtered and the filtrate is evaporated in vacuo. Trituration of the residue with Et2O provides a white solid (50 mg.). The solid is taken up in EtOAc (5 ml.) and filtered. The EtOAc filtrate is extracted with saturated aqueous NaHCO3 (3 × 2 ml.). The combined extracts are acidified to pH 2 with 10% HCl and extracted with EtOAc (4 × 3 ml.). The EtOAc extracts are washed with brine, dried over MgSO4, filtered, and evaporated in vacuo to yield 7-(2-thienylacetamido)-6-methoxy-3-acetoxymethyl-ceph-3-em-4-carboxylic acid (34 mg.) as a white solid.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated in vacuo
  3. customTrituration of the residue with Et2O provides a white solid (50 mg.)
  4. filtrationfiltered
  5. extractionThe EtOAc filtrate is extracted with saturated aqueous NaHCO3 (3 × 2 ml.)
  6. extractionextracted with EtOAc (4 × 3 ml.)
  7. washThe EtOAc extracts are washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-79eed847047949b0a1c1d0c1c9f52ab3
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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