HCID 131714214, compound → HCID 131714213, compound

HRID 648845Notes

Reaction equation

HRID 648845 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:39]1[N:40]=[CH:41][S:42][CH:43]=1)[C:12]([NH:14][CH:15]1[C:37](=[O:38])[N:17]2[C:18]([C:24]([O:26]CC3C=CC([N+]([O-])=O)=CC=3)=[O:25])=[C:19]([O:22][CH3:23])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.O1CCCC1.C(O)(=O)C.[Pd]>[C:1]([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:39]1[N:40]=[CH:41][S:42][CH:43]=1)[C:12]([NH:14][CH:15]1[C:37](=[O:38])[N:17]2[C:18]([C:24]([OH:26])=[O:25])=[C:19]([O:22][CH3:23])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 1

HCID 131714214HCID 131714214, compound

Product 1

HCID 131714213HCID 131714213, compoundYield 74.9%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-methoxy-3-cephem-4-carboxylate (syn isomer) (2.9 g) was dissolved in a mixed solution of methanol (50 ml), tetrahydrofuran (30 ml) and glacial acetic acid (0.5 ml). After adding 10% palladium on carbon (1.5 g) to the solution, the mixture was subjected to catalytic reduction at ambient temperature under atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. Water and ethyl acetate were added to the residue and the mixture was adjusted to pH 7.5 with a saturated aqueous solution of potassium carbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer) (1.71 g).

Workup

  1. customwas subjected to catalytic reduction at ambient temperature under atmospheric pressure
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater and ethyl acetate were added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-0cdd9327f8894e82a712da91f5e7b9de
Source dataset
uspto-grants-1988_04
Patent number
US04736039

Reaction notes

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