Ethanol → HCID 131714967, compound

HRID 1731705Notes

Reaction equation

HRID 1731705 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:34]1[N:35]=[C:36]([NH:39][C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])[S:37][CH:38]=1)[C:5]([NH:7][CH:8]1[C:32](=[O:33])[N:10]2[C:11]([C:19]([O:21]CC3C=CC([N+]([O-])=O)=CC=3)=[O:20])=[C:12]([CH2:15][S:16][CH:17]=[CH2:18])[CH2:13][S:14][C@H:9]12)=[O:6].[H][H].C(O)C.P([O-])([O-])([O-])=O>[Pd].O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:34]1[N:35]=[C:36]([NH:39][C:40](=[O:45])[C:41]([F:43])([F:42])[F:44])[S:37][CH:38]=1)[C:5]([NH:7][CH:8]1[C:32](=[O:33])[N:10]2[C:11]([C:19]([OH:21])=[O:20])=[C:12]([CH2:15][S:16][CH:17]=[CH2:18])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

7

Reactant 4

HCID 702EthanolHCID 1061PhosphateHCID 131714968HCID 131714968, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131714967HCID 131714967, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl 7-[2-methoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-vinylthiomethyl-3-cephem-4-carboxylate (syn isomer) (100 mg) was hydrogenated in the presence of 5% palladium on carbon under an atmospheric pressure of hydrogen in a mixture of tetrahydrofuran (6 ml), ethanol (0.6 ml) and 0.025M phosphate buffer solution (pH 6.85, 6.4 ml) at ambient temperature for 1.5 hours. 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 diluted hydrochloric acid. The aqueous layer was separated, adjusted to pH 6 with diluted hydrochloric acid, washed with ethyl acetate, adjusted to pH 2.4 with diluted 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 diethyl ether to give 7-[2-methoxyimino-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}acetamido]-3-vinylthiomethyl-3-cephem-4-carboxylic acid (syn isomer) (30.0 mg).

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 diethyl ether

Sources & evidence

ORD record
ord-499426e4409642fa9036141686ec779a
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

Loading…