7-Aminocephalosporanic acid → HCID 70455521, compound

HRID 1284636Notes

Reaction equation

HRID 1284636 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:15]([SH:16])=[N:14][N:13]=[N:12]2)[CH2:4][CH2:3]1.CC(O[CH2:21][C:22]1[CH2:31][S:30][C@@H:25]2[C@H:26]([NH2:29])[C:27](=[O:28])[N:24]2[C:23]=1[C:32]([OH:34])=[O:33])=O.C(=O)(O)[O-].[Na+]>O>[NH2:29][CH:26]1[C:27](=[O:28])[N:24]2[C:23]([C:32]([OH:34])=[O:33])=[C:22]([CH2:21][S:16][C:15]3[N:11]([CH2:10][CH2:9][CH2:8][N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[N:12]=[N:13][N:14]=3)[CH2:31][S:30][C@H:25]12

Participants

5

Reactant 3

HCID 4413287-Aminocephalosporanic acidHCID 516892Sodium Bicarbonate2×HCID 178480872HCID 178480872, compound

Product 1

HCID 70455521HCID 70455521, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
64 °C

Procedure

To a solution of 1-[3-(4-methyl-1-piperazinyl)propyl]-1H-tetrazole-5-thiol.dihydrochloide (75.32 g) in water (6 l) was added 7-aminocephalosporanic acid (60.0 g) and the mixture was adjusted to pH 5.4 with a saturated aqueous solution of sodium bicarbonate and stirred for 2 hours at 64° C. The reaction mixture was cooled and adjusted to pH 6.84 with a saturated aqueous solution of sodium bicarbonate. The resulting mixture was subjected to column chromatography (CM-Cephadex, H-type: 3 l), eluting with water, 0.5% aqueous solution of sodium chloride and 2% aqueous solution of sodium chloride. The fiactions containing the object compound were collected. The resulting mixture (about 7 l) was adjusted to pH 4.5 with a saturated aqueous solution of sodium bicarbonate and then subjected to column chromatography (Non-ion adsorption resin, Diaion HP 20 prepared by Mitsubishi Chemical Industries: 3l) and eluting with water, 2% isopropyl alcohol and 15% isopropyl alcohol. The fractions containing the object compound were collected and then concentrated. The concentrate was lyophilized to give a powder of 7-amino-3-[1-[3-(4-methyl-1-piperazinyl)propyl]-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (34.6 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washeluting with water, 0.5% aqueous solution of sodium chloride and 2% aqueous solution of sodium chloride
  3. additionThe fiactions containing the object compound
  4. customwere collected
  5. customsubjected to column chromatography (Non-ion adsorption resin, Diaion HP 20 prepared by Mitsubishi Chemical Industries: 3l)
  6. washeluting with water, 2% isopropyl alcohol and 15% isopropyl alcohol
  7. additionThe fractions containing the object compound
  8. customwere collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c17c68ce3fc54e0794b4babc22f98bef
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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