Dimethylformamide → Diphenylmethyl 3-azidomethyl-7-(imidazol-2-yl)aminoceph-3-em-4-carboxylate hydrochloride

HRID 2118583Notes

Reaction equation

HRID 2118583 reaction equation
[NH2:1][CH:2]1[C:29](=[O:30])[N:4]2[C:5]([C:13]([O:15][CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[C:6]([CH2:9][N:10]=[N+:11]=[N-:12])[CH2:7][S:8][C@H:3]12.[ClH:31].F[C:33]1[NH:34][CH:35]=[CH:36][N:37]=1.C(#N)C.CN(C=O)C>C(Cl)Cl>[ClH:31].[N:10]([CH2:9][C:6]1[CH2:7][S:8][C@@H:3]2[CH:2]([NH:1][C:33]3[NH:34][CH:35]=[CH:36][N:37]=3)[C:29](=[O:30])[N:4]2[C:5]=1[C:13]([O:15][CH:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:14])=[N+:11]=[N-:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 126246272-Fluoro-1H-imidazole hydrochlorideHCID 131715212Diphenylmethyl 7-amino-3-azidomethylceph-3-em-4-carboxylate

Product 1

HCID 131715210Diphenylmethyl 3-azidomethyl-7-(imidazol-2-yl)aminoceph-3-em-4-carboxylate hydrochlorideYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of diphenylmethyl 7-amino-3-azidomethylceph-3-em-4-carboxylate (1.2 g.), 2-fluoroimidazole hydrochloride (367 mg.) and acetonitrile (4 ml.) was stirred at 85°. When a complete solution was achieved DMF (1 ml.) was added. After 2 hours the solvent was evaporated and the residue, after drying overnight, was purified by chromatography on fine mesh silica (ratio 40:1 w/w) at 0° using methylene chloride/MeOH/HOAc 100:0:0 to 92:4:4 v/v/v as eluant. The oil obtained was dissolved in the minimum of methylene chloride and precipitated with ether. After drying there was obtained diphenylmethyl 3-azidomethyl-7-(imidazol-2-yl)aminoceph-3-em-4-carboxylate hydrochloride (38%) as a white powder having the following n.m.r. in solent A: 3.65 (d, 1H); 3.8 (d, 1H); 3.95 (d, 1H); 4.3 (d, 1H); 5.3 (d, 1H); 5.85 (d, 1H); 6.9 (s, 2H); 7.0 (s, 1H); 7.5-7.7 (m, 10H).

Workup

  1. additionwas added
  2. customAfter 2 hours the solvent was evaporated
  3. customthe residue, after drying overnight
  4. customwas purified by chromatography on fine mesh silica (ratio 40:1 w/w) at 0°
  5. customThe oil obtained
  6. customprecipitated with ether
  7. customAfter drying there

Sources & evidence

ORD record
ord-c77e2e605bfe47b8b6425e9e67fe6ed2
Source dataset
uspto-grants-1987_07
Patent number
US04678781

Reaction notes

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