O-Phenylenediamine → HCID 70508553, compound

HRID 1463154Notes

Reaction equation

HRID 1463154 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([N:30]=[C:31](Br)Br)[C:28](=[O:34])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].[C:35]1([NH2:42])[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH2:41]>C1COCC1>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31]3[NH:41][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[N:42]=3)[C:28](=[O:34])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 88691128HCID 88691128, compound

Product 1

HCID 70508553HCID 70508553, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diphenylmethyl 3-acetoxymethyl-7-dibromomethyleneaminoceph-3-em-4-carboxylate (0.608 g., 1 mmole) in THF stirred under nitrogen at ambient temperature was added orthophenylenediamine (0.216 g., 2 mmole) in THF and the reaction was allowed to continue stirring for 4 hours. The solution was then evaporated to dryness and the residue was dissolved in CH2Cl2 containing a little methanol. This solution was chromatographed on silica gel (50 g.) at -40° using CH2Cl2 /MeOH 85:15 v/v as eluant to give diphenylmethyl 3-acetoxymethyl-7-(benzimidazol-2-yl)aminoceph-3-em-4-carboxylate (0.39 g.). The product had the following n.m.r. spectrum in CDCl3 : 1.92(s,3H); 3.25(m,2H); 4.57(d,1H); 4.97(d,1H); 5.15(d,1H); 5.90(d,1H); 6.85(s,1H); 3.25(m,10H).

Workup

  1. customThe solution was then evaporated to dryness
  2. dissolutionthe residue was dissolved in CH2Cl2 containing a little methanol
  3. customThis solution was chromatographed on silica gel (50 g.) at -40°

Sources & evidence

ORD record
ord-546be85b17604520b920796b3843d5c7
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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