Sodium Carbonate → Benzhydryl 7-phenylacetamido-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate

HRID 464224Notes

Reaction equation

HRID 464224 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Br-].[CH:10]([O:23][C:24]([C:26]1[N:31]2[C:32](=[O:44])[CH:33]([NH:34][C:35](=[O:43])[CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@H:30]2[S:29][CH2:28][C:27]=1[CH2:45][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(OCC)(=O)C>[C:37]1([CH2:36][C:35]([NH:34][CH:33]2[C:32](=[O:44])[N:31]3[C:26]([C:24]([O:23][CH:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[O:25])=[C:27]([CH:45]=[CH:1][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)[CH2:28][S:29][C@H:30]23)=[O:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 103713-PyridinecarboxaldehydeHCID 11430Potassium CarbonateHCID 88669831HCID 88669831, compound

Product 1

HCID 131714373Benzhydryl 7-phenylacetamido-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylateYield 48.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Nicotinaldehyde (32.1 g) was added to a solution of [4-benzhydryloxycarbonyl-7-(2-phenylacetamido)-3-cephem-3-ylmethyl]triphenylphosphonium bromide (84.0 g) in a mixture of tetrahydrofuran (800 ml) and water (400 ml) and the solution was adjusted to pH 9.0 with 20% aqueous sodium carbonate. The solution was stirred at ambient temperature for 2 hours under keeping the pH 8.8 to 9.2 with 20% aqueous potassium carbonate. Ethyl acetate (800 ml) and water (800 ml) were added to the resulting solution. The separated organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography using a mixture of acetone and dichloromethane (1:1 U/U) as eluent. The eluted fraction was evaporated to give benzhydryl 7-(2-phenylacetamido)-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylate (cis-trans mixture) (28.5 g).

Workup

  1. washThe separated organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product obtained by concentration
  4. customwas purified by silica gel column chromatography
  5. additiona mixture of acetone and dichloromethane (1:1 U/U) as eluent
  6. customThe eluted fraction was evaporated

Sources & evidence

ORD record
ord-6dfc34c57152456f80476c987c7ad21f
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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