Ethanol → HCID 178436976, compound

HRID 2351149Notes

Reaction equation

HRID 2351149 reaction equation
[N+](C1C=CC(C[O:9][C:10]([CH2:12][O:13][N:14]=[C:15]([C:43]2[N:44]=[C:45]([NH:48][C:49](=[O:54])[C:50]([F:53])([F:52])[F:51])[S:46][CH:47]=2)[C:16]([NH:18][CH:19]2[C:41](=[O:42])[N:21]3[C:22]([C:28]([O:30]CC4C=CC([N+]([O-])=O)=CC=4)=[S:29])=[C:23]([CH:26]=[CH2:27])[CH2:24][S:25][C@H:20]23)=[O:17])=[O:11])=CC=1)([O-])=O.C(O)C.P([O-])([O-])([O-])=O.[H][H]>[Pd].O1CCCC1>[C:10]([CH2:12][O:13][N:14]=[C:15]([C:43]1[N:44]=[C:45]([NH:48][C:49](=[O:54])[C:50]([F:51])([F:52])[F:53])[S:46][CH:47]=1)[C:16]([NH:18][CH:19]1[C:41](=[O:42])[N:21]2[C:22]([C:28]([OH:30])=[S:29])=[C:23]([CH:26]=[CH2:27])[CH2:24][S:25][C@H:20]12)=[O:17])([OH:11])=[O:9]

Participants

7

Reactant 4

HCID 702EthanolHCID 1061PhosphateHCID 131716165HCID 131716165, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178436976HCID 178436976, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl 7-[2-(p-nitrobenzyloxycarbonylmethoxyimino)-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-vinylthio-3-cephem-4-carboxylate (syn isomer) (2.3 g) was hydrogenated in the presence of 5% palladium on carbon in a mixture of tetrahydrofuran (100 ml), ethanol (11.5 ml) and 0.025M phosphate buffer solution (pH 6.85) (125 ml) at ambient temperature for 5 hours under 1 atmospheric pressure of hydrogen. The catalyst was filtered off and washed with ethyl acetate and a saturated aqueous solution of sodium bicarbonate successively. The filtrate and washings were combined and adjusted to pH 8 with dilute hydrochloric acid. The aqueous layer was separated, adjusted to pH 6 with dilute hydrochloric acid and washed with ethyl acetate. The aqueous layer was adjusted to pH 2 with dilute hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated in vacuo and triturated with diisopropyl ether to give 7-[2-carboxymethoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-vinylthio-3-cephem-4-carboxylic acid (syn isomer) (1.05 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. customThe aqueous layer was separated
  4. washwashed with ethyl acetate
  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. concentrationconcentrated in vacuo
  9. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-9d4dd50c2d4e4538adb501d01d39b302
Source dataset
uspto-grants-1989_10
Patent number
US04871730

Reaction notes

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