HCID 131713433, compound → HCID 131713432, compound

HRID 1650920Notes

Reaction equation

HRID 1650920 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][CH:8]=[O:9])=[N:4][C:3]=1[C:10](=[N:37][O:38][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:11]([NH:13][CH:14]1[C:35](=[O:36])[N:16]2[C:17]([C:22]([O:24]CC3C=CC([N+]([O-])=O)=CC=3)=[O:23])=[C:18]([Cl:21])[CH2:19][S:20][C@H:15]12)=[O:12]>CO.O1CCCC1.C(O)(=O)C.[C].[Pd]>[Cl:1][C:2]1[S:6][C:5]([NH:7][CH:8]=[O:9])=[N:4][C:3]=1[C:10](=[N:37][O:38][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:11]([NH:13][CH:14]1[C:35](=[O:36])[N:16]2[C:17]([C:22]([OH:24])=[O:23])=[C:18]([Cl:21])[CH2:19][S:20][C@H:15]12)=[O:12]

Participants

6

Reactant 1

HCID 131713433HCID 131713433, compound

Product 1

HCID 131713432HCID 131713432, compoundYield 80.1%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl 7-[2-(5-chloro-2-formamidothiazol-4-yl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer) (6.2 g) was dissolved in a mixed solution of methanol (60 ml), tetrahydrofuran (40 ml) and glacial acetic acid (0.5 ml). After adding 10% palladium carbon (3.1 g) to the solution, the mixture was subjected to catalytic reduction at room temperature under atmospheric pressure. The catalyst was filtered off, and the filterate was concentrated under reduced pressure. Water and ethyl acetate were added to the residue and the mixture was adjusted to pH 7.5 with saturated aqueous sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extract layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated to give 7-[2-(5-chloro-2-formamidothiazol-4-yl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer) (4.03 g).

Workup

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

Sources & evidence

ORD record
ord-7efc0047768442019cfa59d3f61f613d
Source dataset
uspto-grants-1990_05
Patent number
US04925948

Reaction notes

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