HCID 131713921, compound → HCID 131713920, compound

HRID 1632756Notes

Reaction equation

HRID 1632756 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:37][O:38][CH3:39])[C:8]([NH:10][CH:11]2[C:35](=[O:36])[N:13]3[C:14]([C:18]([O:20][CH2:21][C:22]([O:24]CC4C=CC([N+]([O-])=O)=CC=4)=[O:23])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[H][H]>[Pd].O1CCCC1.CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:37][O:38][CH3:39])[C:8]([NH:10][CH:11]2[C:35](=[O:36])[N:13]3[C:14]([C:18]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 2

HCID 131713921HCID 131713921, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131713920HCID 131713920, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-nitrobenzyloxycarbonylmethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.34 g) and 10% palladium on carbon (0.7 g) in tetrahydrofuran (50 ml) and methanol (15 ml) was subjected to catalytic reduction under hydrogen atmosphere at 1 atm., until the uptake of hydrogen ceased. After removing the insoluble substance by filtration, the filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate to give powder (0.35 g) of carboxymethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer), mp>250° C.

Workup

  1. customAfter removing the insoluble substance
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-9001e12d9ba4484cbf8f1f220db92361
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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