Triethylamine → HCID 178502645, compound

HRID 1463151Notes

Reaction equation

HRID 1463151 reaction equation
[NH2:1][CH:2]1[C:30](=[O:31])[N:4]2[C:5]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:6]([CH:10]=[N:11][O:12][CH3:13])[C@@H:7]([CH3:9])[S:8][C@H:3]12.CCN(CC)CC.[Cl:39][CH2:40][C:41]([NH:43][C:44]1[S:45][CH:46]=[C:47](/[C:49](=[N:53]/[O:54][CH3:55])/[C:50](Cl)=[O:51])[N:48]=1)=[O:42]>C(Cl)Cl>[Cl:39][CH2:40][C:41]([NH:43][C:44]1[S:45][CH:46]=[C:47](/[C:49](=[N:53]/[O:54][CH3:55])/[C:50]([NH:1][CH:2]2[C:30](=[O:31])[N:4]3[C:5]([C:14]([O:16][CH:17]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:15])=[C:6]([CH:10]=[N:11][O:12][CH3:13])[C@@H:7]([CH3:9])[S:8][C@H:3]23)=[O:51])[N:48]=1)=[O:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12884124HCID 12884124, compoundHCID 131713618HCID 131713618, compound

Product 1

HCID 178502645HCID 178502645, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 656 mg of diphenylmethyl 7-amino-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylate in 30 ml of CH2Cl2 were added, at -20° C., 0.2 ml of Et3N and 407 mg of 2-(2-chloroacetylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetylchloride, and the mixture was stirred at from -20° C. to -15° C. for 1.5 hours. The reaction solution was washed with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl solution, successively, and dried over MgSO4, followed by distilling off the CH2Cl2 under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.AcOEt (15:1) were collected to distill off the solvent under reduced pressure, thus yielding 783 mg (75%) of diphenylmethyl 7-[2-(2-chloroacetylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-2α-methyl-3-methoxyiminomethylceph-3-em-4-carboxylate.

Workup

  1. washThe reaction solution was washed with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl solution
  2. dry with materialsuccessively, and dried over MgSO4
  3. distillationby distilling off the CH2Cl2 under reduced pressure
  4. additionThe residue was added on a column of silica gel
  5. washthe fractions eluted with CH2Cl2
  6. customAcOEt (15:1) were collected
  7. distillationto distill off the solvent under reduced pressure

Sources & evidence

ORD record
ord-03f78c43781c41c59b4797792da66edb
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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