Water → HCID 59536771, compound
Reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([NH:15]C(=O)OC(C)(C)C)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.ClS([N:27]=[C:28]=[O:29])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[C:28](=[O:29])([O:1][CH2:2][CH2:3][CH:4]([NH2:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)[NH2:27]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Of the compound from Example 128A, 827 mg (2.59 mmol) were introduced in 100 ml of acetonitrile. A solution of 676 μl (7.77 mmol) of chlorosulphonyl isocyanate in 10 ml of acetonitrile was added dropwise at −15° C. After 5 min, 50 ml of water were added and the mixture was then stirred at 60° C. overnight. The reaction mixture was admixed with saturated aqueous sodium hydrogen carbonate solution and then extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. Drying of the residue in an HV gave 678 mg (quant.) of the title compound.
Workup
- extractionextracted three times with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- customfreed from the solvent on a rotary evaporator
- customDrying of the residue in an HV
Sources & evidence
- ORD record
- ord-601bf9f0a44a4bad8ed70cd71b44e568
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796324B2
Reaction notes
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