Phosphoric Acid → HCID 70474055, compound

HRID 1415410Notes

Reaction equation

HRID 1415410 reaction equation
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12.C([O-])(O)=O.[Na+].C(N1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35])(OCC)=O.OP(O)(O)=O>CC(C)=O.O>[C:26]1(=[O:35])[N:1]([CH:2]2[C:13](=[O:14])[N:4]3[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]23)[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]12

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 31187N-CarbethoxyphthalimideHCID 516892Sodium BicarbonateHCID 13475828(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 70474055HCID 70474055, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a suspension of 181 g. of 7-amino-3-methyl-3-cephem-4-carboxylic acid (7-ADCA) in 1700 ml. of water, 142 g. of NaHCO3 were slowly added followed by a solution of 186 g. of N-carbethoxyphthalimide in 1 liter of acetone added dropwise over a 30 minute period. After stirring for 3 hrs. the solution was cooled in an ice-water bath and acidified to pH 2.1 by addition of 600 ml. of 42.5% of H3PO4. The resulting precipitate was filtered, washed with water, and vacuum dried to give 227 g. of a mixture of the starting material and the desired phthalimido compound. The mixture was separated by extraction with warm acetone and ethyl acetate, recovering 105 g. of 7-ADCA. The yield of the phthalimido compound was 114 g. A sample (1 g.) of product was crystallized from acetone (15 ml.); colorless crystals, m.p. 223°-225°; [α]D + 428.02° (MeCN); ir (nujol) 1810, 1785, 1740 and 1710 cm-1 ; nmr (CDCl3) δ 2.38 (s, 3, CH3), 3.0 and 3.75 (ABq, 2, J=14 Hz), 5.13 (d, 1, J=4.5 Hz), 5.71 (d, 1, J=4.5 Hz), and 7.82 (m, 4, ArH).

Workup

  1. additionTo a suspension of 181 g
  2. temperaturethe solution was cooled in an ice-water bath
  3. additionacidified to pH 2.1 by addition of 600 ml
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water, and vacuum
  6. customdried
  7. customto give 227 g
  8. additionof a mixture of the starting material
  9. customThe mixture was separated by extraction with warm acetone and ethyl acetate
  10. customrecovering 105 g
  11. customA sample (1 g.) of product was crystallized from acetone (15 ml.)
  12. custom[α]D + 428.02° (MeCN)

Sources & evidence

ORD record
ord-372b716fe94441b39745a81c9887f5c4
Source dataset
uspto-grants-1977_01
Patent number
US04005074

Reaction notes

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