Chlorosulfonyl isocyanate → HCID 14326680, compound
Reaction equation
[O:1]=[C:2]1[C@@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][NH:3]1.[Cl:17][S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19]>C(OCC)(=O)C>[Cl:17][S:18]([NH:21][C:22]([N:3]1[CH2:4][C@H:5]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:2]1=[O:1])=[O:23])(=[O:20])=[O:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 1.76 g (0.008 mol) of (S)-(2-oxo-3-azetidinyl)carbamic acid, phenylmethyl ester in 80 ml of ethyl acetate was added 0.7 ml (0.008 mol) of chlorosulfonyl isocyanate at room temperature for 1 hour to yield a solution of (S)-[1-[[(chlorosulfonyl)amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester. The solution was cooled to 0° C. and a solution of silylated 2-amino-4,5-dihydroxybenzoic acid, prepared from 1.35 g (0.008 mol of 2-amino-4,5-dihydroxybenzoic acid in 80 ml of ethyl acetate by the addition of 4.45 ml (0.024 mol) of N-methyl-N-(trimethylsilyl)trifluoroacetamide and warming to 50° C. for 60 minutes, was added dropwise. The reaction mixture was stirred overnight at room temperature. Then ice water (~200 ml) was added and stirring was continued for an additional 30 minutes. The two phases were separated, the aqueous phase was layered with ethyl acetate and acidified to pH 2 (2N hydrochloric acid). The organic phase was dried and evaporated. On treatment with ether, 2.4 g of a solid residue was obtained.
Sources & evidence
- ORD record
- ord-36a398472c004b00afe4a39fab1ef2e3
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04801705
Reaction notes
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