3-(Trimethylsilyl)oxazolidin-2-one → 7-Aminodeacetoxycephalosporanic acid
Reaction equation
C[Si](C)(C)[N:3]1[CH2:7][CH2:6][O:5][C:4]1=[O:8].C1(C)[CH:16]=[CH:15][C:14]([S:17](O)(=O)=O)=CC=1.[CH2:22]([N:24](CC)CC)[CH3:23].C1(C)C=CC(S(O)(=O)=[O:36])=CC=1.CN(C)C1C=CC=CC=1.NC(N)=S>>[CH3:16][C:15]1[CH2:14][S:17][C@@H:23]2[C@H:22]([NH2:24])[C:4](=[O:8])[N:3]2[C:7]=1[C:6]([OH:36])=[O:5]Participants
Procedure
To the above solution, there were added 0.28 mole of 3-trimethylsilyl-2-oxazolidinone (TMSO, 38.2 ml) and 0.02 mole of triethylamine p-toluenesulphonate (8.468 g). After stirring for 15 minutes, the mixture was heated under reflux for 120 minutes. Thereafter 0.1 mole of dimethylaniline p-toluene sulphonate (29.3 g) and 0.12 mole of thiourea (9.13 g) were added and heating was maintained for a further 60 minutes. Thereafter the mixture was concentrated at reduced pressure and water (100 ml) was added to the residue. The pH was adjusted to 8.5 in the presence of methylene chloride, the phenyl-pseudothio-hydantoin was filtered out and the water phase was decanted off. After further adjustment To pH 4.2, the mixture was filtered again to give 7-ADCA (14.9 g) with 70% yield. Identified by its IR spectrum, m.p. 232- 42 (d) and [α] D2 = 105.0° (C = 1%, 0.5 N HCL).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 120 minutes
- temperatureheating
- temperaturewas maintained for a further 60 minutes
- concentrationThereafter the mixture was concentrated at reduced pressure and water (100 ml)
- additionwas added to the residue
- filtrationthe phenyl-pseudothio-hydantoin was filtered out
- customthe water phase was decanted off
- filtrationAfter further adjustment To pH 4.2, the mixture was filtered again
Sources & evidence
- ORD record
- ord-fab4856869f84449bf843e1ee6bcab46
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04058660
Reaction notes
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