Methanol → HCID 20432356, compound

HRID 2412493Notes

Reaction equation

HRID 2412493 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([F:27])[N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[CH3:28][OH:29]>>[F:27][C:5]1[N:6]([C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[C:3]([CH2:2][O:29][CH3:28])[N:4]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 20432342HCID 20432342, compound

Product 1

HCID 20432356HCID 20432356, compound

Procedure

4-Chloromethyl-2-fluoro-1-triphenylmethylimidazole was dissolved in MeOH, and allowed to stand 1 hour, giving 2-fluoro-4-methoxymethyl-1-triphenylmethylimidazole. This was reacted at 60° for 3 hours in CHCl3 /MeOH solution with t-butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylate in the presence of toluene-p-sulphonic acid, and the product purified by chromatography to give t-butyl 3-acetoxymethyl-7-(4-methoxymethylimidazol-2-yl)aminoceph-3-em-4-carboxylate, having the following n.m.r. spectrum in d6DMSO: 1.5 (s, 9H); 2.05 (s, 3H); 3.3 (s, 3H); 3.5 (d, 1H); 3.7 (d, 1H); 4.3 (s, 2H); 4.7 (d, 1H); 5.0 (d, 1H); 5.2 (d, 1H); 5.7 (d, 1H); 7.1 (s, 1H).

Sources & evidence

ORD record
ord-efe5ee6321394c8483e5765a38c6f5bf
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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