Triethylamine → HCID 177710556, compound

HRID 1463147Notes

Reaction equation

HRID 1463147 reaction equation
CCN(CC)CC.[Cl:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:22]/[O:23][CH3:24])/[C:19](Cl)=[O:20])[N:17]=1)=[O:11].[NH2:25][CH:26]1[C:55](=[O:56])[N:28]2[C:29]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:30]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@H:31]([CH3:33])[S:32][C@H:27]12>C(Cl)Cl>[Cl:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16](/[C:18](=[N:22]/[O:23][CH3:24])/[C:19]([NH:25][CH:26]2[C:55](=[O:56])[N:28]3[C:29]([C:39]([O:41][CH:42]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)=[O:40])=[C:30]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@H:31]([CH3:33])[S:32][C@H:27]23)=[O:20])[N:17]=1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12884124HCID 12884124, compoundHCID 70504140HCID 70504140, compound

Product 1

HCID 177710556HCID 177710556, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0.5 ml portion of Et3N, along with 1.13 g of 2-(2-chloroacetylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetyl chloride, was added to a solution of 1.6 g of diphenylmethyl 7-amino-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate in 50 ml of CH2Cl2 at -40° C., and the mixture was stirred at from -20° C. to -15° C. for 45 minutes. The reaction solution was washed with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl solutions, 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 (5:1) were collected to distill off the solvent, thus yielding 1.5 g (61%) of diphenylmethyl 7-[2-(2-chloroacetylaminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-2β-methyl-3-acetoxymethylceph-3-em-4-carboxylate.

Workup

  1. washThe reaction solution was washed with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl solutions
  2. dry with materialdried 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 (5:1) were collected
  7. distillationto distill off the solvent

Sources & evidence

ORD record
ord-90a125400fc44def99341aaaf62b221d
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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