Hydrochloric Acid → HCID 131714500, compound

HRID 1284637Notes

Reaction equation

HRID 1284637 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:41]2[N:42]=[C:43]([NH:46]C=O)[S:44][CH:45]=2)[C:9]([NH:11][CH:12]2[C:39](=[O:40])[N:14]3[C:15]([C:36]([OH:38])=[O:37])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH2:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1.Cl.C(=O)(O)[O-].[Na+]>CO>[CH:1]1([O:6][N:7]=[C:8]([C:41]2[N:42]=[C:43]([NH2:46])[S:44][CH:45]=2)[C:9]([NH:11][CH:12]2[C:39](=[O:40])[N:14]3[C:15]([C:36]([OH:38])=[O:37])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH2:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131714501HCID 131714501, compound

Product 1

HCID 131714500HCID 131714500, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-[3-(4-methyl-1-piperazinyl)propyl]-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.1 g), methanol (85 ml) and conc.hydrochloric acid (0.6 ml) was stirred for 45 minutes at room temperature. The reaction mixture was adjusted to pH 4.5 with a saturated aqueous solution of sodium bicarbonate and then concentrated. The concentrate was adjusted to pH 7 with a saturated aqueous solution of sodium bicarbonate and then subjected to column chromatography (CM-cephadex, H-type: 110 ml), eluted with 1%, 2%, 4% and 5% aqueous solution of sodium chloride The fractions containing the object compound were collected and adjusted to pH 4.3 with a saturated aqueous solution of sodium bicarbonate. The resulting solution was subjected to column chromatography (Non-ion adsorption resin, Diaion HP20 prepared by Mitsubishi Chemical Industries: 50 ml), eluting with water and 20% isopropyl alcohol. The fractions containing the object compound were collected and concentrated under reduced pressure. The concentrate was lyophilized to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-[3-(4-methyl-1-piperazinyl)propyl]-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.3 g).

Workup

  1. concentrationconcentrated
  2. washeluted with 1%, 2%, 4% and 5% aqueous solution of sodium chloride The fractions
  3. additioncontaining the object compound
  4. customwere collected
  5. customThe resulting solution was subjected to column chromatography (Non-ion adsorption resin, Diaion HP20 prepared by Mitsubishi Chemical Industries: 50 ml)
  6. washeluting with water and 20% isopropyl alcohol
  7. additionThe fractions containing the object compound
  8. customwere collected
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27eb0ef83f2e448ab866c76117bd5c9f
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

Loading…