Salicylaldehyde → 4-Methoxybenzyl 7 beta-(2-hydroxybenzylideneamino)-3-chloromethyl-ceph-3-em-4-carboxylate

HRID 1742050Notes

Reaction equation

HRID 1742050 reaction equation
Cl.[NH2:2][C@@H:3]1[C:24](=[O:25])[N:5]2[C:6]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12.[CH:26](=O)[C:27]1[C:28](=[CH:30][CH:31]=[CH:32][CH:33]=1)[OH:29].C(N(CC)CC)C>CO>[OH:29][C:28]1[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=1[CH:26]=[N:2][C@@H:3]1[C:24](=[O:25])[N:5]2[C:6]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 8471TriethylamineHCID 140320244-methoxybenzyl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride (1:1)

Product 1

HCID 1366141604-Methoxybenzyl 7 beta-(2-hydroxybenzylideneamino)-3-chloromethyl-ceph-3-em-4-carboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 50 ml of methanol was dissolved 4.05 g(10 mmol) of 4-methoxybenzyl 7 β-amino-3-chloromethyl-ceph-3-em-4-carboxylate hydrochloride, and 1.28 ml(12 mmol) of salicylaldehyde and 1.39 ml(10 mmol) of triethylamine were added thereto. The reaction mixture was stirred for 5 hours. The resulting precipitate was filtered, washed with 50 ml of methanol and dried to give 4.26 g of the desired compound(90%).

Workup

  1. additionwere added
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with 50 ml of methanol
  4. customdried

Sources & evidence

ORD record
ord-fb3e1e6c7aa7480ca0a82dd33d70dbdf
Source dataset
uspto-grants-1994_08
Patent number
US05336673

Reaction notes

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