Water → HCID 68646332, compound
Reaction equation
[OH:1][CH2:2][C@:3]([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)[CH3:4].[Cl:23]S([N:27]=[C:28]=[O:29])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[ClH:23].[C:28](=[O:29])([O:1][CH2:2][C@:3]([NH2:15])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)[CH3:4])[NH2:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 520 mg (1.63 mmol) of the compound from Example 70A in 10 ml of acetonitrile was cooled to −15° C. and admixed with 198 μl (2.28 mmol) of chlorosulphonyl isocyanate. After 10 min, 18 ml of water were added and the mixture was heated at 60° C. overnight. After cooling to RT, the solution was rendered alkaline by addition of saturated aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvents on a rotary evaporator. For complete deprotection of the amino group, the residue was admixed with 5 ml of a 4M solution of hydrogen chloride in dioxane, and this mixture was stirred at RT for 5 min and concentrated on a rotary evaporator. Drying of the residue in an HV gave the title compound (440 mg, 90% of theory).
Workup
- temperatureAfter cooling to RT
- extractionextracted three times with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- customfreed from the solvents on a rotary evaporator
- concentrationconcentrated on a rotary evaporator
- customDrying of the residue in an HV
Sources & evidence
- ORD record
- ord-dd65c2d87c954c70b721e4da036359ab
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202895B2
Reaction notes
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