Phosgene → 2-Oxo-1,3-oxazolidine-3-carbonyl chloride
Reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[C:7](Cl)([Cl:9])=[O:8].C(N(CC)CC)C.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>O1CCCC1.C(Cl)Cl>[O:6]=[C:2]1[N:3]([C:7]([Cl:9])=[O:8])[CH2:4][CH2:5][O:1]1Participants
Procedure
In a similar manner to that of Example 1-9), 2-oxo-3-oxazolidinecarbonyl chloride, which was prepared from 2-oxazolidinone (1.04 g), phosgene (0.018 mole) and triethylamine (3.0 g) in tetrahydrofuran was treated with a solution of 7-(D-2-phenylglycinamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (3.0 g) and bis(trimethylsilyl) acetamide (4.8 g) in methylene chloride (60 ml). The reaction mixture was worked up in a similar manner to that of Example 1--1) to give powder (1.92 g). This powder was dissolved into acetone and water was added thereto. The resultant mixture was concentrated, and a precipitated solid was collected by filtration to give powder (1.55 g) of 7-[D-2-(2-oxo-3-oxazolidinecarboxamido)-2-phenylacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, mp 165° to 170° C. (dec).
Sources & evidence
- ORD record
- ord-4437dde9fdd649b4b8820c62e1509620
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04172198
Reaction notes
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