Sodium borohydride → HCID 20432395, compound
Reaction equation
[F:1][C:2]1[N:3]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1.[BH4-].[Na+]>C1COCC1.C(O)(C)C>[F:1][C:2]1[N:3]([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Fluoro-4-formyl-1-triphenylmethylimidazole was dissolved in a 2:1 (v/v) mixture of THF and isopropanol and treated with sodium borohydride at 20°. After 5 minutes the reaction was quenched with water. Extractive work-up and final trituration with MeOH gave 2-fluoro-4-hydroxymethyl-1-triphenylmethylimidazole. This was reacted with methanesulphonyl chloride and triethylamine in CH2Cl2 at ambient temperature to give 4-chloromethyl-2-fluoro-1-triphenylmethylimidazole. This was treated at ambient temperature in a water/THF solution with sodium azide, and crude product deprotected with toluene-p-sulphonic acid in CH2Cl2, to give 4-azidomethyl-2-fluoroimidazole as its toluene-p-sulphonate salt. This was reacted at 60° for 4 hours in DMF with t-butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylate. The product was purified by silica gel chromatography at -20°, using as eluant CH2Cl2 /MeOH/HOAc 96:2:2 v/v/v, to give t-butyl 3-acetoxymethyl-7-(4-azidomethylimidazol-2-yl)aminoceph-3-em-4-carboxylate, having the following i.r. spectrum: νmax (film) 1680; 1725; 1745; 1790; 2110 cm-1.
Workup
- customAfter 5 minutes the reaction was quenched with water
Sources & evidence
- ORD record
- ord-644571aaf90042db94f5057bf65af84c
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04492692
Reaction notes
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